Triethylamine → N-(Butan-2-yl)-N-methyl-1-phenylisoquinoline-3-carboxamide

HRID 615387

Reaction equation

HRID 615387 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([C:17](O)=[O:18])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(OCC)=O.[CH3:33][NH:34][CH:35]([CH2:37][CH3:38])[CH3:36]>C(Cl)(Cl)Cl>[CH3:33][N:34]([CH:35]([CH3:36])[CH2:37][CH3:38])[C:17]([C:9]1[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[C:11]([CH:10]=1)=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 111026N-Methyl-2-butanamineHCID 4078961-Phenylisoquinoline-3-carboxylic acid

Product 1

HCID 13272363N-(Butan-2-yl)-N-methyl-1-phenylisoquinoline-3-carboxamideYield 63.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Operations are carried out as for Example 7, starting with 2.96 g of 1-phenyl isoquinoline 3-carboxylic acid, 1.33 g of triethylamine, 1.49 g of ethyl chloroformate and 1.34 g of N-methyl 2-butanamine in 120 ml of chloroform. 2.4 g of N-methyl N(1-methyl propyl) 1-phenyl isoquinoline 3-carboxamide melting at 95°-96° C., are obtained.

Sources & evidence

ORD record
ord-b729fd781ac7454fb621227a888506ed
Source dataset
uspto-grants-1985_02
Patent number
US04499094

Linked notes

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