Benzaldehyde → 1-[4-(4-Benzylpiperazin-1-yl)phenyl]ethanone

HRID 885880Notes

Reaction equation

HRID 885880 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CCOC(C)=O>[CH2:16]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][C:10]([C:13](=[O:15])[CH3:14])=[CH:11][CH:12]=2)[CH2:2][CH2:3]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 97269Piperazin-4-ylacetophenoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 7578081-[4-(4-Benzylpiperazin-1-yl)phenyl]ethanoneYield 54.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(4-piperazin-1-yl-phenyl)-ethanone (500 mg, 2.45 mmol), benzaldehyde (312 mg, 2.94 mmol) and NaBH(OAc)3 (778 mg, 3.67 mmol) in AcOEt (15 ml) was stirred at room temperature overnight. The resulting solution was partitioned between water and DCM and the organic phase was dried over Na2SO4 and evaporated in vacuo. The crude product was purified by silica gel chromatography (eluent: DCM/MeOH/NH4OH 95:5:0.2) to give 390 mg of 1-[4-(4-benzyl-piperazin-1-yl)-phenyl]-ethanone.

Workup

  1. customThe resulting solution was partitioned between water and DCM
  2. dry with materialthe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customThe crude product was purified by silica gel chromatography (eluent: DCM/MeOH/NH4OH 95:5:0.2)

Sources & evidence

ORD record
ord-b8e8179a00464bc988c4bee90f5f1b3b
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

Loading…