5-Amino-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline → (+/-) N-(1,2-Dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-5-chloro-4-ethoxy-2-methoxybenzamide, hydrochloride

HRID 650961Notes

Reaction equation

HRID 650961 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:13])[CH:7]2[CH3:12].[Cl:14][C:15]1[C:16]([O:26][CH2:27][CH3:28])=[CH:17][C:18]([O:24][CH3:25])=[C:19]([CH:23]=1)[C:20](O)=[O:21]>>[ClH:14].[CH3:12][CH:7]1[C:8]2[C:3](=[C:2]([NH:1][C:20](=[O:21])[C:19]3[CH:23]=[C:15]([Cl:14])[C:16]([O:26][CH2:27][CH3:28])=[CH:17][C:18]=3[O:24][CH3:25])[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:5][N:6]1[CH3:13]

Participants

3

Reactant 2

HCID 217104395-Amino-1,2-dimethyl-1,2,3,4-tetrahydroisoquinolineHCID 217104695-Chloro-4-ethoxy-2-methoxybenzoic acid

Product 1

HCID 70682955(+/-) N-(1,2-Dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-5-chloro-4-ethoxy-2-methoxybenzamide, hydrochloride

Procedure

The title compound was prepared in a similar fashion to Example 1 from 5-amino-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline and 5-chloro-4-ethoxy-2-methoxybenzoic acid. The crude product was recrystallised from methanol and ethyl acetate to afford a pale brown solid (319 mg).

Workup

  1. customThe crude product was recrystallised from methanol and ethyl acetate

Sources & evidence

ORD record
ord-78087190b33f4027a950cba0efc9b5b8
Source dataset
uspto-grants-2001_08
Patent number
US06277861B1

Reaction notes

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