1-Methyl-4-piperidyl benzilate → 1-[2-(4-Benzyloxycarbonyl-phenyl)-ethyl]-4-(2-hydroxy-2,2-diphenyl-acetoxy)-1-methyl-piperidinium bromide

HRID 551382Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9](=[O:24])[C:10]([OH:23])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.[CH2:25]([O:32][C:33](=[O:43])[C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][Br:42])=[CH:36][CH:35]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[Br-:42].[CH2:25]([O:32][C:33]([C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][N+:2]2([CH3:1])[CH2:3][CH2:4][CH:5]([O:8][C:9](=[O:24])[C:10]([OH:23])([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:6][CH2:7]2)=[CH:36][CH:35]=1)=[O:43])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Hydroxy-diphenyl-acetic-acid-1-methyl-piperidin-4-yl-ester (1.56 g, 4.8 mmol) and 4-(2-bromo-ethyl)-benzoic acid benzyl ester (2.3 ml, 7.21 mmol) are dissolved in DMF (5 ml) and stirred at 50° C. for 20 hours, followed by heating at 60° C. for 5 hours. Concentration and purification twice by C-18 reverse phase chromatography (eluant: water/acetonitrile) gives the title compound as a mixture of diastereoisomers.

Workup

temperatureby heating at 60° C. for 5 hours
concentrationConcentration and purification twice by C-18 reverse phase chromatography (eluant: water/acetonitrile)

Sources & evidence

ORD record: ord-77a6d129e3944751ac8ef906c6b29df7
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947730B2

Reaction notes

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