Triethylamine → 2(R)-ethyl 1-[(1-phenyl 3-isoquinolyl) carbonyl]piperidine

HRID 615408

Reaction equation

HRID 615408 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.Cl.[CH2:34]([C@@H:36]1[CH2:41][CH2:40][CH2:39][CH2:38][NH:37]1)[CH3:35]>C1(C)C=CC=CC=1>[CH2:34]([C@@H:36]1[CH2:41][CH2:40][CH2:39][CH2:38][N:37]1[C:17]([C:9]1[N:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:16]2[C:11]([CH:10]=1)=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:18])[CH3:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4078961-Phenylisoquinoline-3-carboxylic acidHCID 18596119(R)-2-Ethylpiperidine hydrochloride

Product 1

HCID 248426822(R)-ethyl 1-[(1-phenyl 3-isoquinolyl) carbonyl]piperidineYield 57.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Operations are carried out as for Example 7, starting from 2.5 g of 1-phenyl isoquinoline 3-carboxylic acid, 2.86 g of triethylamine, 1.24 g of ethyl chloroformate and 1.93 g of 2(R)-ethyl piperidine hydrochloride in 100 ml of toluene. After chromatography, 2 g of 2(R)-ethyl 1-[(1-phenyl 3-isoquinolyl) carbonyl]piperidine in the form of oil are obtained. αD26 =+1.4° (2% in ethanol).

Sources & evidence

ORD record
ord-4e313db4a4574cf1a2f5d32a6112034f
Source dataset
uspto-grants-1985_02
Patent number
US04499094

Linked notes

Loading…