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All 3 posts Subject: Phenylalkylamines & Mannich Bases Please login to post Down

Natrix
(Hive Bee)
01-16-03 20:35
No 398791
      Phenylalkylamines & Mannich Bases

Synthesis of Mannich Bases Using Substituted Aromatic Alcohols with Secondary Amines:
Relative Reactivity and Regioselectivity Depending on Substrates
Ki-Whan Chi , Yoon Soo Ahn, Tae Ho Park , Jeong Soo Ahn, Hyun Ah Kim, Joo Yeon Park
Journal of the Korean Chemical Society 45(1), 51-60 (2001) (http://newjournal.kcsnet.or.kr/main/j_search/j_jkcs_archives_view2.htm?code=K010107)

Abstract
One-pot Mannich reaction of substituted hydroxy aromatic compounds with secondary amines in an aprotic solvent has been studied. The results demonstrate that the relative reactivity and regioselectivity of the Mannich reaction depend on the steric hindrance of amines as well as the nucleophilicity of hydroxy aromatic rings.

Rhodium
(Chief Bee)
01-16-03 20:45
No 398795
User Picture       mannich bases to phenethylamines

Reminds me of these:

https://www.rhodium.ws/chemistry/2cb.mannich.html
https://www.rhodium.ws/chemistry/mescaline.mannich.html

Rhodium
(Chief Bee)
09-15-04 05:23
No 531394
User Picture       Synthesis of PEAs from Phenylacetonitriles
(Rated as: excellent)

Synthesis of Phenethylamines from Phenylacetonitriles
_{Obtained by Alkylation of Cyanide Ion with Mannich Bases from Phenols and Other Benzylamines}
J. H. Short, D. A. Dunnigan and C. W. Ours
Tetrahedron 29, 1931-1939 (1973) (https://www.rhodium.ws/pdf/pea.mannich.bncn.pdf)

Abstract
Benzylamines, obtained by the Mannich reaction on phenols or by reductive alkylation of aldehydes, have been used in place of benzyl chlorides to alkylate cyanide ion to obtain nitriles which may be reduced to phenethylamines. Yields of 4-hydroxy-3-methoxyphenylacetonitrile were about the same from the primary, secondary, and tertiary amines. Benzylamines not having either an ortho or para OH group did not function as alkylating agents. With such compounds it was necessary to prepare the quaternary salts before alkylation could be achieved. 6-Hydroxydopamine was prepared from 2,4,5-trimethoxybenzaldehyde utilizing the latter approach. 3,5-Dimethoxy-4-hydroxyphenethylamine was cyclized to the corresponding dihydroisoquinoline. The isoquinoline and tetrahydroisoquinoline analogs were also prepared. 4-Hydroxy-3-methoxyphenylacetonitrile was hydrolysed to homovanillic acid, the naturally occurring metabolite of dopamine.

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	All 3 posts		Subject: Phenylalkylamines & Mannich Bases		Please login to post		Down


		Natrix (Hive Bee) 01-16-03 20:35 No 398791				Phenylalkylamines & Mannich Bases
						Synthesis of Mannich Bases Using Substituted Aromatic Alcohols with Secondary Amines: Relative Reactivity and Regioselectivity Depending on Substrates Ki-Whan Chi , Yoon Soo Ahn, Tae Ho Park , Jeong Soo Ahn, Hyun Ah Kim, Joo Yeon Park Journal of the Korean Chemical Society 45(1), 51-60 (2001) (http://newjournal.kcsnet.or.kr/main/j_search/j_jkcs_archives_view2.htm?code=K010107) Abstract One-pot Mannich reaction of substituted hydroxy aromatic compounds with secondary amines in an aprotic solvent has been studied. The results demonstrate that the relative reactivity and regioselectivity of the Mannich reaction depend on the steric hindrance of amines as well as the nucleophilicity of hydroxy aromatic rings.



		Rhodium (Chief Bee) 01-16-03 20:45 No 398795				mannich bases to phenethylamines
						Reminds me of these: https://www.rhodium.ws/chemistry/2cb.mannich.html https://www.rhodium.ws/chemistry/mescaline.mannich.html



		Rhodium (Chief Bee) 09-15-04 05:23 No 531394				Synthesis of PEAs from Phenylacetonitriles (Rated as: excellent)
						Synthesis of Phenethylamines from Phenylacetonitriles _{Obtained by Alkylation of Cyanide Ion with Mannich Bases from Phenols and Other Benzylamines} J. H. Short, D. A. Dunnigan and C. W. Ours Tetrahedron 29, 1931-1939 (1973) (https://www.rhodium.ws/pdf/pea.mannich.bncn.pdf) Abstract Benzylamines, obtained by the Mannich reaction on phenols or by reductive alkylation of aldehydes, have been used in place of benzyl chlorides to alkylate cyanide ion to obtain nitriles which may be reduced to phenethylamines. Yields of 4-hydroxy-3-methoxyphenylacetonitrile were about the same from the primary, secondary, and tertiary amines. Benzylamines not having either an ortho or para OH group did not function as alkylating agents. With such compounds it was necessary to prepare the quaternary salts before alkylation could be achieved. 6-Hydroxydopamine was prepared from 2,4,5-trimethoxybenzaldehyde utilizing the latter approach. 3,5-Dimethoxy-4-hydroxyphenethylamine was cyclized to the corresponding dihydroisoquinoline. The isoquinoline and tetrahydroisoquinoline analogs were also prepared. 4-Hydroxy-3-methoxyphenylacetonitrile was hydrolysed to homovanillic acid, the naturally occurring metabolite of dopamine. ^{The Hive - Clandestine Chemists Without Borders}

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