Methanol → 2-{[2-(3-hydroxy-4-methyl-phenyl)-ethylamino]-methyl}-N-(4-phenyl-butyl)-benzamide

HRID 6713Notes

Reaction equation

HRID 6713 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][NH:12][CH2:13][C:14]2[CH:32]=[CH:31][CH:30]=[CH:29][C:15]=2[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])[CH:6]=[CH:7][C:8]=1[CH3:9].B(Br)(Br)Br.CO>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][NH:12][CH2:13][C:14]2[CH:32]=[CH:31][CH:30]=[CH:29][C:15]=2[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 220185252-{[2-(3-methoxy-4-methyl-phenyl)-ethylamino]-methyl}-N-(4-phenyl-butyl)-benzamide

Product 1

HCID 220184772-{[2-(3-hydroxy-4-methyl-phenyl)-ethylamino]-methyl}-N-(4-phenyl-butyl)-benzamideYield 14.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Crude 2-{[2-(3-methoxy-4-methyl-phenyl)-ethylamino]-methyl}-N-(4-phenyl-butyl)-benzamide (derived via Procedure C from 200 mg resin) is dissolved in 3 mL of dichloromethane and treated with 0.5 mL of 1 M of boron tribromide in dichloromethane for 16 h. Methanol (3 mL) is carefully added and the volatiles are removed. The crude residue is purified via semi-preparative HPLC to give 2-{[2-(3-hydroxy-4-methyl-phenyl)-ethylamino]-methyl}-N-(4-phenyl-butyl)-benzamide (28 mg). MS: m/z 417 (m+H).

Workup

  1. customthe volatiles are removed
  2. customThe crude residue is purified via semi-preparative HPLC

Sources & evidence

ORD record
ord-06c14e7ef5bc4b458558b542fc10a30f
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Reaction notes

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