Potassium Carbonate → N-(1-Fluorobenzyl)-N-indan-2-yl-2-(6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl]acetamide

HRID 916882Notes

Reaction equation

Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[CH:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:9][CH2:8][CH2:7]2.[F:22][C:23]1([CH:43]=[CH:42][CH:41]=[CH:40][CH2:39]1)[CH2:24][N:25]([CH:30]1[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31]1)[C:26](=[O:29])[CH2:27]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:22][C:23]1([CH:39]=[CH:40][CH:41]=[CH:42][CH2:43]1)[CH2:24][N:25]([CH:30]1[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31]1)[C:26](=[O:29])[CH2:27][C:10]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:5][C:4]([O:3][CH3:2])=[C:13]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:8][NH:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (160, 153 mg, 0.5 mmol), N-(1-fluorobenzyl)-N-indan-2-yl-2-bromoacetamide (161, 180 mg, 0.5 mmol) and potassium carbonate (500 mg) in acetonitrile is heated at 80° C. overnight. After cooling, the mixture is filtered and concentrated. The resulting residue is purified by column chromatography eluting with 5% methanol in chloroform to provide the title product (162) as a thick oil (215 mg, 78%). 1H NMR (CDCl3) 6.8–7.3 (m, 14H), 6.60(s, 1H), 6.05 (s, 1H),

Workup

temperatureAfter cooling
filtrationthe mixture is filtered
concentrationconcentrated
customThe resulting residue is purified by column chromatography
washeluting with 5% methanol in chloroform

Sources & evidence

ORD record: ord-3aa6506ffe774da2a156d3c9687e50c1
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271270B2

Reaction notes

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