Chloroacetonitrile → Tert-butyl 4-(cyanomethyl)piperazine-1-carboxylate

HRID 1157334Notes

Reaction equation

HRID 1157334 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[CH2:15][C:16]#[N:17]>ClCCl.C(N(CC)CC)C>[C:16]([CH2:15][N:11]1[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]1)#[N:17]

Participants

5

Reactant 2

HCID 7856ChloroacetonitrileHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 21936030Tert-butyl 4-(cyanomethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of N-Boc piperazine (5 g) in dry dichloromethane (100 ml), triethyl amine (10 ml) followed by chloro acetonitrile (25.02 ml) were added dropwise. The reaction mixture was allowed to stir at room temperature for overnight. The solvent was removed under vacuum and residue was diluted with dichloromethane (200 ml). The organic layer was washed with water, brine and concentrated to dryness under reduced pressure to afford tert-butyl 4-(cyanomethyl)piperazine-1-carboxylate, which was used for the next reaction without further purification.

Workup

  1. additionwere added dropwise
  2. customThe solvent was removed under vacuum and residue
  3. additionwas diluted with dichloromethane (200 ml)
  4. washThe organic layer was washed with water, brine
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-59da07b988194e4e8b63c4ceea8f1cf1
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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