Acetic Acid → 3-[(4-methylpiperazin-1-yl)methyl]benzonitrile

HRID 885860Notes

Reaction equation

HRID 885860 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7])=O.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>C(Cl)Cl>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:1][C:3]2[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=2)[C:6]#[N:7])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 90670m-FormylbenzonitrileHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 71646473-[(4-methylpiperazin-1-yl)methyl]benzonitrileYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-formyl-benzonitrile (1.5 g, 11.45 mmol), N-methyl piperazine (1.49 g, 14.9 mmol) and NaBH(OAc)3 (3.63 g, 17.18 mmol) in DCM (75 ml) and CH3COOH (0.851 ml, 14.9 mmol) was stirred overnight at room temperature, 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 97:3:0.5) to give 1.7 g of 3-(4-methyl-piperazin-1-ylmethyl)-benzonitrile.

Workup

  1. washwashed with 1 M Na2CO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customThe crude mixture was purified by column chromatography (eluent: DCM/MeOH/NH4OH 97:3:0.5)

Sources & evidence

ORD record
ord-6fe35290e0624fc9b0ac2bfa56b7a8bb
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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