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

HRID 1157319Notes

Reaction equation

HRID 1157319 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]>C1COCC1.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 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of N-Boc piperazine (1 g) in dry THF (20 ml), triethylamine (3 ml), followed by chloroacetonitrile (5.02 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 ethyl acetate (20 ml). The organic layer was 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. concentrationThe organic layer was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7f645550e2b74a4886aa6b6fc1f29716
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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