Potassium Carbonate → Methyl 2-methyl-2-phenyl-6-{4-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-piperidin-1-yl}-hexanecarboxylate

HRID 1167111

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

0.2 g (0.574 mmol) of 4′-trifluoromethyl-biphenyl-2-carboxylic acid-piperidin-4-yl-amide, 0.15 g (0.5 mmol) of methyl 6-bromo-2-methyl-2-phenyl-hexanecarboxylate and 0.083 g (0.6 mmol) of potassium carbonate are dissolved in 10 ml of acetonitrile. The mixture is stirred for 8 hours at 60° C. and for 14 hours at ambient temperature. Then the reaction mixture is poured onto water and extracted with ethyl acetate. The organic phase is dried over sodium sulphate and the solvent is distilled off in the rotary evaporator. After column chromatography on silica gel (eluant: dichloromethane/methanol=20:1) a highly viscous oil remains.

Workup

additionThen the reaction mixture is poured onto water
extractionextracted with ethyl acetate
dry with materialThe organic phase is dried over sodium sulphate
distillationthe solvent is distilled off in the rotary evaporator

Sources & evidence

ORD record: ord-6cd803da8c144149904d0fa9c1848818
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617325B1

Linked notes

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