Hydrochloric Acid → HCID 86584233, compound

HRID 2288196Notes

Reaction equation

HRID 2288196 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)=[O:7].[C:34](=[O:37])([O-])[O-].[K+].[K+].[ClH:40]>CN(C)C=O.C(OCC)(=O)C>[ClH:40].[ClH:40].[F:31][C:28]([F:29])([F:30])[C:26]1[CH:25]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:32])[F:33])[CH:27]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:3][C:4]#[C:5][CH2:6][N:8]2[CH2:13][CH2:34][O:37][CH2:10][CH2:9]2)[CH2:10][C@H:9]1[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 54095749HCID 54095749, compound

Product 1

HCID 86584233HCID 86584233, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(2-naphthylmethyl)piperazine (200 mg) and 1-(4-chloro-2-butynyl)morpholine hydrochloride (95 mg) in N,N-dimethylformamide (0.5 ml) was stirred at room temperature in the presence of powdered potassium carbonate (177 mg). After 17 hours, the reaction mixture was diluted with ethyl acetate (30 ml) and then washed successively with water and brine, and dried over magnesium sulfate. After evaporation of the solvent in vacuo, the resulting residue was purified by column chromatography on silica gel using ethyl acetate as an eluent. The product obtained was dissolved in ethyl acetate and treated with 4N hydrogen chloride in ethyl acetate solution to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(4-morpholino-2-butynyl)-2-(2-naphthylmethyl)piperazine dihydrochloride (257 mg).

Workup

  1. washwashed successively with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customAfter evaporation of the solvent in vacuo
  4. customthe resulting residue was purified by column chromatography on silica gel
  5. customThe product obtained

Sources & evidence

ORD record
ord-c2fb2eb754144420bea0ff3f7012db68
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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