Water → HCID 19029391, compound

HRID 2256294Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:26])[C:9](=[O:25])[CH2:10][CH:11]([CH2:18][CH2:19]OS(C)(=O)=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[C:27]1([C:33]2([OH:39])[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCOC(C)=O.O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:26])[C:9](=[O:25])[CH2:10][CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:18][CH2:19][N:36]2[CH2:37][CH2:38][C:33]([OH:39])([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:34][CH2:35]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N-(4-Chlorophenyl)-beta-(2-methanesulfonyloxyethyl)-N-methyl-benzenepropanamide (1.44 g) in DMF (10 mL) was treated with 4-phenyl-4-hydroxypiperidine (1.61 g) and the mixture heated at 80° C. for 2 hours. The cooled reaction mixture was diluted the EtOAc (50 mL) and water (50 mL) and the aqueous phase removed. The aqueous layer was extracted with EtOAc (2×50 mL) and the combined organic extracts, washed with water (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give an oil. Silica gel chromatography eluting with 10% MeOH:CH2Cl2 gave the title compound (0.7 g). Mass spectrum (FAB): 477.

Workup

customThe cooled reaction mixture
customthe aqueous phase removed
extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
washthe combined organic extracts, washed with water (50 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give an oil
washSilica gel chromatography eluting with 10% MeOH

Sources & evidence

ORD record: ord-ce30c5096f3e4ce69d63b56475d2e858
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654316

Reaction notes

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