Hydrazine hydrate (1:1) → Tert-butyl 4-(4-aminobutyl)piperidine-1-carboxylate

HRID 1294464Notes

Reaction equation

HRID 1294464 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]2C(=O)C3C(=CC=CC=3)C2=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][CH2:16][CH2:17][NH2:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 184257562-[4-(1-Tertbutoxycarbonylpiperidin-4-yl)-butyl]-isoindol-1,3-dione

Product 1

HCID 18425747Tert-butyl 4-(4-aminobutyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

113.0 g (292 mmol) 2-[4-(1-tert-butoxycarbonylpiperidin-4-yl)-butyl]-isoindol-1,3-dione are dissolved in 600 ml ethanol, added to 29.3 g (585 mmol) hydrazine hydrate and heated to boiling for three hours. After cooling the solution, the mixture is filtered and the filtrate is concentrated under vacuum. The residue is dispersed in the heat (ca. 50° C.) between 500 ml toluene and 500 ml 10% sodium hydroxide solution. The organic phase is washed once with 50 ml 10% sodium hydroxide solution and twice, each with 50 ml water. The solvent is removed under vacuum and the residue is dried at 70° C. under high-vacuum and processed further without additional purification. Yield of colorless oil: 64.0 g (85%).

Workup

  1. temperatureheated
  2. temperatureAfter cooling the solution
  3. filtrationthe mixture is filtered
  4. concentrationthe filtrate is concentrated under vacuum
  5. additionThe residue is dispersed in the
  6. washThe organic phase is washed once with 50 ml 10% sodium hydroxide solution
  7. customThe solvent is removed under vacuum
  8. customthe residue is dried at 70° C. under high-vacuum
  9. customprocessed further without additional purification

Sources & evidence

ORD record
ord-03e219204d034e4ab9f41ae8739f3816
Source dataset
uspto-grants-2007_07
Patent number
US07241745B2

Reaction notes

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