Acetonitrile → 1-tert-Butyloxycarbonyl-4-(3-aminopropyl)piperazine

HRID 1986162Notes

Reaction equation

HRID 1986162 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][N:36]=[N+]=[N-])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C1COCC1.C(#N)C>O>[C:20]([O:24][C:25]([N:27]1[CH2:28][CH2:29][N:30]([CH2:33][CH2:34][CH2:35][NH2:36])[CH2:31][CH2:32]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 86625340Tert-butyl 4-(3-azidopropyl)piperazine-1-carboxylate

Product 1

HCID 177509451-tert-Butyloxycarbonyl-4-(3-aminopropyl)piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triphenylphosphine (2.78 g, 10.6 mmol) is added to a stirred solution of 4-(3-azido-propyl)-piperazine-1-carboxylic acid tert-butyl ester (2.05 g, 7.61 mmol) in a solution of THF (10 mL)/acetonitrile (30 mL)/water (4 mL). The resultant mixture is stirred for 16 hours. After concentration and subsequent chromatography on silica gel, eluting with 2 M NH3/CH3OH in dichloromethane 0-20%, the title compound is obtained as a clear oil (1.76 g, 95% yield).

Workup

  1. concentrationAfter concentration and subsequent chromatography on silica gel
  2. washeluting with 2 M NH3/CH3OH in dichloromethane 0-20%

Sources & evidence

ORD record
ord-28fa504dac5442618d220833fbc392c8
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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