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

HRID 1750727Notes

Reaction equation

HRID 1750727 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([BH3-])#N>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 3

HCID 710273,3-DiphenylacroleinHCID 498716Cyano-borohydrideHCID 2761178Ethyl 4-(piperazin-1-yl)benzoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of ethyl 4-piperazin-1-ylbenzoate (1.36 g) and 3,3-diphenylacrylaldehyde (1.56 g) in dichloromethane (10 mL) and methanol (10 mL) was treated with polymer-supported cyanoborohydride (2.47 mmol/g, 6 g), shaken at room temperature for 24 hours, and filtered. The resin was washed with 1:1 dichloromethane/methanol (10 mL×3) and the combined filtrates were concentrated. The concentrate was purified by silica gel chromatography eluting with a gradient from 10%-50% ethyl acetate/hexanes to provide the desired product.

Workup

  1. filtrationfiltered
  2. washThe resin was washed with 1:1 dichloromethane/methanol (10 mL×3)
  3. concentrationthe combined filtrates were concentrated
  4. customThe concentrate was purified by silica gel chromatography
  5. washeluting with a gradient from 10%-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-cca96db529334ef887db242389c61f87
Source dataset
uspto-grants-2015_10
Patent number
US09156856B2

Reaction notes

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