Acetic Acid → 1-[2-(4-Methyl-piperazin-1-yl-methyl)phenyl]-ethanone

HRID 885857Notes

Reaction equation

HRID 885857 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)(=[O:3])[CH3:2].[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C(Cl)Cl>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[C:1](=[O:3])[CH3:2])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 1526712-AcetylbenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 593125691-[2-(4-Methyl-piperazin-1-yl-methyl)phenyl]-ethanoneYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-acetyl-benzaldehyde (1 g, 6.75 mmol), N-methyl piperazine (878 mg, 8.76 mmol) and NaBH(OAc)3 (2.14 g, 10.12 mmol) in DCM (50 ml) was stirred at room temperature for 1 h and then acetic acid (526 mg, 8.76 mmol) was added. The resulting solution was stirred at room temperature overnight and then diluted with DCM and washed with 1 M Na2CO3. The organic phase was dried over Na2SO4 and evaporated in vacuo. The crude mixture was purified by column chromatography (eluent: DCM/MeOH/NH4OH 95:5:0.2) to give 1.06 g of 1-[2-(4-methyl-piperazin-1-ylmethyl)-phenyl]-ethanone.

Workup

  1. stirringThe resulting solution was stirred at room temperature overnight
  2. washwashed with 1 M Na2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude mixture was purified by column chromatography (eluent: DCM/MeOH/NH4OH 95:5:0.2)

Sources & evidence

ORD record
ord-0849efa8cfb7407f830324150f3e1e02
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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