Potassium Carbonate → Tert-butyl 4-(cyanomethyl)piperazine-1-carboxylate

HRID 1804621Notes

Reaction equation

HRID 1804621 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]#[N:23]>CN(C)C=O>[C:22]([CH2:21][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)#[N:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 21936030Tert-butyl 4-(cyanomethyl)piperazine-1-carboxylateYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2.7 g (15 mmol) of tert-butyl piperazine-1-carboxylate in 30 mL of anhydrous N,N-dimethylformamide was added 2.4 g (17 mmol) of potassium carbonate followed by 2.1 g (17 mmol) of bromoacetonitrile. The resulting heterogeneous mixture was stirred at ambient temperature of 12 h, quenched with water then extracted with ethyl acetate. The combined organic layers were washed with water then brine, dried over magnesium sulfate and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography eluting with a 0-75% acetone in hexanes gradient to afford the title compound as clear gum (1.0 g, 30%). 1H-NMR (500 MHz, CDCl3) δ 3.53 (s, 2H), 3.48 (t, J=5.0 Hz, 4H), 2.53 (t, J=5.0 Hz, 4H), 1.45 (s, 9H). LC-MS: m/z (ES) 226.2 (MH)+.

Workup

  1. customquenched with water
  2. extractionthen extracted with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. customevaporated to dryness in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a 0-75% acetone in hexanes gradient

Sources & evidence

ORD record
ord-92a72abafab24326b32b989a65af4ede
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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