Triethylamine → 4-Nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxylate

HRID 876235Notes

Reaction equation

[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][NH:14][CH2:13][CH:12]([NH:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:34](Cl)(=[O:45])[O:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1.C(=O)(O)[O-].[Na+]>ClCCl.O>[C:18]1([C:17]([NH:16][CH:12]2[CH2:11][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:25])[F:26])=[CH:9][CH:8]=3)[CH2:15][N:14]([C:34]([O:35][C:36]3[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=3)=[O:45])[CH2:13]2)=[O:24])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C., 200 mg (0.55 mmol) of N-{5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzamide and 153 μl (1 l mmol) of triethylamine were initially charged in 17 ml of dichloromethane, and 111 mg (0.55 mmol) of 4-nitrophenyl chlorocarbonate were added slowly. The mixture was stirred at 0° C. for 2 h and then warmed to RT. Water and saturated aqueous sodium bicarbonate solution were added, and the reaction mixture was extracted. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. The crude product was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 254 mg (87% of theory)

Workup

temperaturewarmed to RT
extractionthe reaction mixture was extracted
dry with materialThe organic phase was dried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe crude product was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record: ord-c19d8255e5eb45bc857d6a87472ed558
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987248B2

Reaction notes

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