Acetic Acid → 2-Methoxyphenyl-4-[3-(cyclohexanecarbonyl)-3-(phenyl)propyl]piperazine

HRID 1789994Notes

Reaction equation

HRID 1789994 reaction equation
[CH:1]1([C:7](=[O:18])[CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH:10]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[CH:1]1([C:7](=[O:18])[CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH2:10][N:30]2[CH2:29][CH2:28][N:27]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[O:20][CH3:19])[CH2:32][CH2:31]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 13461-(2-Methoxyphenyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 120510643-Cyclohexanecarbonyl-3-phenylpropionaldehyde

Product 1

HCID 155240262-Methoxyphenyl-4-[3-(cyclohexanecarbonyl)-3-(phenyl)propyl]piperazineYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.84 g of Compound 5c and 1.19 g of 1-(2-methoxyphenyl)-piperazine in 30 ml of dichloromethane, 1.48 g of sodium triacetoxyborohydride and 0.98 ml of acetic acid were added and the resulting mixture was stirred at r.t. for 5 h. After overnight resting, the organic layer was washed with excess of 1M NaOH then with water, dried (Na2SO4) and the solvent was evaporated under vacuum. The crude was purified by flash chromatography eluting with petroleum ether-EtOAc 7:3 to give 1.45 g (99%) of the title compound.

Workup

  1. waitAfter overnight resting
  2. washthe organic layer was washed with excess of 1M NaOH
  3. dry with materialwith water, dried (Na2SO4)
  4. customthe solvent was evaporated under vacuum
  5. customThe crude was purified by flash chromatography
  6. washeluting with petroleum ether-EtOAc 7:3

Sources & evidence

ORD record
ord-6dd37b3ea8d64736b1e8a46281be986b
Source dataset
uspto-grants-2006_07
Patent number
US07071197B2

Reaction notes

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