Water → HCID 131724159, compound

HRID 478408Notes

Reaction equation

HRID 478408 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C:13]([N:15]2[CH2:20][CH2:19][C@H:18]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C@H:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:16]2)=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:42][C:43]([N:45]([CH3:47])[CH3:46])=[O:44].O>CN(C)C=O>[F:34][C:2]([F:33])([F:1])[C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1)[C:13]([N:15]1[CH2:20][CH2:19][C@H:18]([N:21]2[CH2:26][CH2:25][N:24]([CH2:42][C:43]([N:45]([CH3:47])[CH3:46])=[O:44])[CH2:23][CH2:22]2)[C@H:17]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:16]1)=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 131724158HCID 131724158, compound

Product 1

HCID 131724159HCID 131724159, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Rac-cis-(3,5-Bis-trifluoromethyl-phenyl)-(3-phenyl-4-piperazin-1-yl-piperidin-1-yl)-methanone (200 mg, 0.41 mmol) was dissolved in N,N-dimethylforamide (5 mL). Potassium carbonate (171 mg, 1.24 mmol) and 2-chloro-N,N-dimethylacetamide (0.042 mL, 0.41 mmol) were added and the reaction mixture was stirred at room temperature overnight. Water (50 mL) was added and the mixture was extracted twice with 100 mL ethyl acetate. Organic phases were pooled, dried with magnesium sulfate and evaporated. Chromatography on silica gel with methylen chloride/methanol/triethyl amine 90:10:1 gave the desired product (200 mg, 85%) as an off-white solid, MS: m/e=571.1 (M+H+).

Workup

  1. extractionthe mixture was extracted twice with 100 mL ethyl acetate
  2. dry with materialdried with magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-97188239031c44838578472b34ba2381
Source dataset
uspto-grants-2003_11
Patent number
US06642226B2

Reaction notes

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