Water → tert-Butyl 4-cyanopiperazine-1-carboxylate

HRID 400445Notes

Reaction equation

HRID 400445 reaction equation
[C:1](Br)#[N:2].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].CCN(C(C)C)C(C)C.O>ClCCl>[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:1]#[N:2])[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 14068968tert-Butyl 4-cyanopiperazine-1-carboxylateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3.76 g bromcyane was added to 6 g piperazine-1-carboxylic acid tert-butyl ester and 6.3 mL DIPEA in 30 mL dichlormethane at 0° C. The reaction was stirred 1.5 h at 0° C. Water and dichlormethane was added and the layers were separated. The organic layer was washed with brine and water and evaporated to give 6.8 g of the desired product.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine and water
  3. customevaporated

Sources & evidence

ORD record
ord-2afb461737ab4519b1c24934a05f4261
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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