Hydrazine hydrate (1:1) → tert-Butyl 4-aminopiperazine-1-carboxylate

HRID 1904588Notes

Reaction equation

HRID 1904588 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:12][CH2:13]Cl)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].O.[NH2:16][NH2:17].[Cl-].[NH4+]>>[NH2:16][N:17]1[CH2:13][CH2:12][N:4]([C:5]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:11])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 25517Ammonium ChlorideHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Product 1

HCID 22029174tert-Butyl 4-aminopiperazine-1-carboxylate

Procedure

Under an inert atmosphere at ambient temperature, 15.3 g of the product of Step A and 80 ml of hydrazine hydrate were mixed together and then 150 ml of a saturated aqueous solution of ammonium chloride were added. Extraction was done with methylene chloride and the organic phase was washed with an aqueous solution of ammonium chloride, dried, and the solvent was eliminated under reduced pressure. After chromatography on silica (eluent:methylene chloride - methanol, 100/7) 5 g of the expected product were obtained.

Workup

  1. extractionExtraction
  2. washthe organic phase was washed with an aqueous solution of ammonium chloride
  3. customdried

Sources & evidence

ORD record
ord-70d1a06436e74387b84703caec85fc7f
Source dataset
uspto-grants-1989_06
Patent number
US04839358

Reaction notes

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