Hydrazine hydrate (1:1) → tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylate

HRID 54546Notes

Reaction equation

HRID 54546 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2C(=O)C3=CC=CC=C3C2=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15851771N-[2-[1-tert-butoxycarbonylpiperidin-4-yl]ethyl]phthalimide

Product 1

HCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylateYield 62.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[2-[1-tert-butoxycarbonylpiperidin-4-yl]ethyl]phthalimide (1.0 g) and hydrazine hydrate (0.16 ml) in ethanol (10 ml) was refluxed for 1 hour. After cooling to room temperature, the mixture was evaporated. The residue was chromatographed on alumina eluting with chloroform and the fractions containing the object product were collected and evaporated to give 2-[1-tert-butoxycarbonylpiperidin-4-yl]ethylamine (0.4 g) as an oil.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customthe mixture was evaporated
  3. customThe residue was chromatographed on alumina eluting with chloroform
  4. additionthe fractions containing the object product
  5. customwere collected
  6. customevaporated

Sources & evidence

ORD record
ord-244ecb7a5d654232b725c3ca8bac957d
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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