p-Anisoyl chloride → N-[(R)-2-(1-Isopropylpiperidine-4-ylmethoxy)-1-phenylethyl]-4-methoxybenzamide hydrochloride

HRID 32447Notes

Reaction equation

HRID 32447 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][O:11][CH2:12][C@H:13]([NH2:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH3:21][O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([Cl:29])=[O:28])=[CH:25][CH:24]=1>>[ClH:29].[CH:1]([N:4]1[CH2:5][CH2:6][CH:7]([CH2:10][O:11][CH2:12][C@H:13]([NH:20][C:27](=[O:28])[C:26]2[CH:30]=[CH:31][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 69309716HCID 69309716, compound

Product 1

HCID 69310552N-[(R)-2-(1-Isopropylpiperidine-4-ylmethoxy)-1-phenylethyl]-4-methoxybenzamide hydrochloride

Procedure

Using coupling method B, (R)-2-(1-isopropylpiperidin-4-ylmethoxy)-1-phenylethylamine (150 mg, 0.54 mmol) and 4-methoxybenzoyl chloride (0.12 mL, 1.0 mmol) afforded, after purification (SiO2: 4:2:1 DCM:EtOAc:isopropyl-amine) and conversion to the HCl salt by general method A, 205 mg (91%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 4:2:1 DCM:EtOAc:isopropyl-amine) and conversion to the HCl salt by general method A, 205 mg (91%) of the title compound

Sources & evidence

ORD record
ord-1610803d9b924dcd9e0249952dc4e700
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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