Acetic Acid → Ethyl 4-(4-(3,3-diphenylallyl)piperazin-1-yl)benzoate

HRID 1968599Notes

Reaction equation

HRID 1968599 reaction equation
[N:1]1([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:18]1([C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:25][CH:26]=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CO>[C:18]1([C:24]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:25][CH2:26][N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][CH:17]=3)[CH2:6][CH2:5]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 710273,3-DiphenylacroleinHCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67144443Ethyl 4-(4-(3,3-diphenylallyl)piperazin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of EXAMPLE 1B (6.27 g, 26.8 mmol) and 3,3-diphenylacrylaldehyde (7.26 g, 34.8 mmol) in dichloromethane/methanol (30 mL/30 mL) was added acetic acid (0.6 mL) followed by addition of sodium triacetoxyborohydride (8.52 g, 40.2 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature. The organic solvents were concentrated in vacuo and the residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was washed with water and with brine, dried over magnesium sulfate, filtered and the solvent was evaporated in vacuo. The remaining residue was crystallized from acetonitrile.

Workup

  1. concentrationThe organic solvents were concentrated in vacuo
  2. customthe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. washThe organic layer was washed with water and with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customThe remaining residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-1b22667426394426b49da8807d1a94cd
Source dataset
uspto-grants-2013_04
Patent number
US08426422B2

Reaction notes

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