Tert-butyl 4-(cyanomethyl)piperazine-1-carboxylate → (Piperazin-1-yl)acetonitrile

HRID 1433070Notes

Reaction equation

HRID 1433070 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[N:16])[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N:11]1([CH2:14][C:15]#[N:16])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 1

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

Product 1

HCID 15522031(Piperazin-1-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

To a solution of 30% TFA/CH2Cl2 (10 mL) is added 4-cyanomethyl-piperazine-1-carboxylic acid tert-butyl ester (1.7 g, 6.8 mmol) and the reaction is stirred for 14 h. The reaction is concentrated and chromatoghraphed using silica gel (%1 NH4OH/7% MeOH/CH2Cl2) to isolate piperazin-1-yl-acetonitrile as the free base. 1H NMR (300 MHz, CDCl3) δ4.36 (s, 2H), 3.54 (s, 2H), 3.45 (t, 2H), 3.13 (t, 2H).

Workup

  1. concentrationThe reaction is concentrated

Sources & evidence

ORD record
ord-1a9aad594c9642aca47fad30e4a5a0b2
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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