Water → tert-Butyl 4-({3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}carbonyl)piperazine-1-carboxylate

HRID 876281Notes

Reaction equation

HRID 876281 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.Cl[C:28]([N:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]1)=[O:29].C(N(CC)CC)C.O>ClCCl>[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:28]([N:30]3[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:34][CH2:35]3)=[O:29])[CH2:13]2)=[O:24])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11334154Tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylateHCID 66701272N-{5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzamide

Product 1

HCID 86662379tert-Butyl 4-({3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}carbonyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 220 mg (0.55 mmol) of N-{5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzamide were initially charged in 3 ml of dichloromethane, and 273 mg (1.10 mmol) of tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylate and 116 μl (0.82 mmol) of triethylamine were added. The mixture was slowly warmed to RT overnight. Water was added, and the reaction mixture was extracted. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure. The residue was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 88 mg (28% of theory)

Workup

  1. extractionthe reaction mixture was extracted
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-fa5579aded4d492992cb9deb40cbff23
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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