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Water → HCID 86584250, compound

HRID 2288217
Notes
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Reaction equation

HRID 2288217 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][Cl:18])[CH2:10][C@H:9]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([CH3:27])[CH:21]=1)=[O:7].[CH:37]1([N:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[ClH:18].[ClH:18].[ClH:18].[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][N:46]2[CH2:47][CH2:48][N:43]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)[CH2:44][CH2:45]2)[CH2:10][C@H:9]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([CH3:27])[CH:21]=1)=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 872981-Cyclohexylpiperazine2×HCID 53806279HCID 53806279, compound

Product 1

HCID 86584250HCID 86584250, compoundYield 226.9%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-(4-chloro-2-butynyl)piperazine (200 mg), 1-cyclohexylpiperazine (63 mg) and powdered potassium carbonate (210 mg) in dry N,N-dimethylformamide (2 ml) was stirred for 12 hours at room temperature. Additional 1-cyclohexylpiperazine (25 mg) was added and after 2 hours the reaction mixture was poured into water (20 ml) and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the resulting residue was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol (30:1). The obtained product was dissolved in ethyl acetate and treated with 4N hydrogen chloride in ethyl acetate solution (0.6 ml) to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[4-(4-cyclohexylpiperazin-1-yl)-2-butynyl]piperazine trihydrochloride (220 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe resulting residue was purified by column chromatography on silica gel using
  6. additiona mixture of dichloromethane and methanol (30:1)
  7. dissolutionThe obtained product was dissolved in ethyl acetate
  8. additiontreated with 4N hydrogen chloride in ethyl acetate solution (0.6 ml)

Sources & evidence

ORD record
ord-7a8474a3d42c4667b34df42824578f02
Source dataset
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06087357

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes