112108-01-7

Usage

InChI:InChI=1/C19H20ClNO.ClH/c1-21-9-8-13-10-16(20)18(22)11-15(13)19-14-5-3-2-4-12(14)6-7-17(19)21;/h2-5,10-11,17,19,22H,6-9H2,1H3;1H/t17-,19+;/m0./s1

Upstream product

• 447-53-0 1,2-Dihydronaphthalene 
• 39834-40-7 trans-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol 
• 2018-87-3 (+/-)-trans-1,2-dibromo-1,2,3,4-tetrahydronaphthalene 
• 119-64-2 tetralin 
• 2461-34-9 1,2-epoxy-3,4-dihydronaphthalene 
• 3490-06-0 N-methylhomoveratrylamine 
• 1056246-70-8 2-bromo-1-tetralone 

Downstream Products

• 847265-00-3 6,6aS,7,8,9,13bR-hexahydro-7-methyl-11-nitro-N-phenylmethyl-5H-benzo[d]naphth[2,1-b]azepin-12-amine 

Relevant academic research and scientific papers

Catalytic enantioselective synthesis of the dopamine D1 antagonist ecopipam

A concise asymmetric synthesis of the potent dopamine D1 antagonist, ecopipam, has been accomplished in six steps with 33% overall yield via catalytic enantioselective aziridination and subsequent one-pot Friedel-Crafts cyclization of an in situ generated tethered aziridine with high diastereo- and enantioselectivities.

Novel stereoselective syntheses of the fused benzazepine dopamine D1 antagonist (6as,13br)-11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-5h-benzo[d]naphth[2,1-b] azepin-12-ol (sch 39166): 1. aziridinium salt based syntheses

Several novel enantioselective syntheses of the dopamine D1 antagonist (6aS,13bR)-11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-5H-benzo[d]naphth[2,1-b] azepin-12-ol (2) are described in which the key intermediate was 1-(2,2-dimethoxyethyl)-1-methyl-1a,2,3,7b-tetrahydro-1H-naphth[1,2-b]aziridinium salt (20). The latter species was prepared either from 1-(2,2-dimethoxyethyl)-1a,2,3,7b-tetrahydro-1H-naphth[1,2-b]-azirine (18) by methylation or from the tertiary amino alcohols 1-[(2,2-dimethoxyethyl)methylamino]-1,2,3,4-tetrahydro-2-naphthalenol (23) or 2-[(2,2-dimethoxyethyl)methylamino]-1,2,3,4-tetrahydro-1-naphthalenol (24) by tosylation and in situ ring closure. Regioselective trapping of 20 with Grignard reagent (4-chloro-3-methoxyphenyl)magnesium bromide (10) then afforded the trans amine 1-(4-chloro-3-methoxyphenyl)-N-(2,2-dimethoxyethyl)-1,2,3,4-tetrahydro-N-methyl- 2-naphth-alenamine (22), which was cyclized to give 11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-12-methoxy-5H-benzo[d]-naphth[2,1-b] azepine (9), a known precursor of 2. Several enantioselective syntheses, including a Jacobsen epoxidation route, a de no novo synthesis from L-homophenylalanine, and a classical salt resolution sequence, were developed for the preparation of the key intermediates in chiral form.

Synthesis and receptor affinities of some conformationally restricted analogues of the dopamine D1 selective ligand (5R)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-ol

The synthesis of a structurally novel series of 6,6a,7,8,9,13b-hexahydro-5H-benzo[d]naphtho[2,1-b]azepines (2), conformationally restricted analogues of the dopamine D1 antagonist (5R)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazep