Potassium Carbonate → HCID 9822640, compound

HRID 2188349Notes

Reaction equation

HRID 2188349 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:17])[CH2:15]Br)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18]([C:25]1([OH:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH2:18]([C:25]1([OH:31])[CH2:30][CH2:29][N:28]([CH2:15][C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:8][CH:9]=2)=[O:17])[CH2:27][CH2:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 981524-Benzyl-4-piperidinolHCID 15428811N-(4-cyclohexyl-phenyl)-2-bromoacetamide

Product 1

HCID 9822640HCID 9822640, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of N-(4-cyclohexyl-phenyl)-2-bromoacetamide (29.6 mg, 0.10 mmol), 4-benzyl-4-hydroxypiperidine (19.1 mg, 0.10 mmol), and potassium carbonate (13.8 mg, 0.1 mmol) in dimethyl sulfoxide (1.0 mL) was stirred 1 hour. The mixture was filtered through a short pad of Celite in a pasteur pipet TLC Rf 0.21 (silica gel, 50:50 hexane/ethyl acetate), 0.14 (reverse phase, 80:20 methanol/water); HPLC: 5.89 min (C18 Cartridge column (Perkin Elmer/PE Xpress #0258-0164) 20:80 Acetonitrile/water to 95:5 acetonitrile/water); LC-MS: 407 (M+H+). The filtrate was tested directly in the in vitro biological assays.

Workup

  1. filtrationThe mixture was filtered through a short pad of Celite in a pasteur pipet TLC Rf 0.21 (silica gel, 50:50 hexane/ethyl acetate), 0.14 (reverse phase, 80:20 methanol/water)
  2. custom5.89 min (C18 Cartridge column (Perkin Elmer/PE Xpress #0258-0164) 20:80 Acetonitrile/water to 95:5 acetonitrile/water)

Sources & evidence

ORD record
ord-68ec4e86d42c4e98918b3b4b22464a1e
Source dataset
uspto-grants-2002_06
Patent number
US06410792B1

Reaction notes

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