Water → HCID 178511576, compound

HRID 2354007Notes

Reaction equation

HRID 2354007 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH-](O[C:23]([CH3:25])=O)(OC(C)=O)OC(C)=O.[Na+].O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([C@H:25]3[CH2:23][CH2:6][C@H:1]([NH2:7])[CH2:2][CH2:3]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 178511576HCID 178511576, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.1 g (25.3 mmol) of 4-dibenzylcyclohexanone was dissolved in 50 mL of dichloromethane and stirred for 12 h at RT with 7.4 g (25.3 mmol) of N-phenylpyperazine and 7.4 g (35 mmol) of NaBH(OAc)3. Then water and potassium carbonate were added, the org. phase was separated off, dried and the solvent was eliminated in vacuo. The residue was purified over a silica gel column (ethyl acetate 80/methanol 20+0.5% conc. ammonia). Yield: 1.7 g (15.8%) of cis-isomer and 0.27 (2.5%) of trans-isomer.

Workup

  1. customphase was separated off
  2. customdried
  3. customThe residue was purified over a silica gel column (ethyl acetate 80/methanol 20+0.5% conc. ammonia)

Sources & evidence

ORD record
ord-6044f2dc27c141409793ad05b3e9ced1
Source dataset
uspto-grants-2010_07
Patent number
US07750152B2

Reaction notes

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