Hydroxylamine → TERT-BUTYL 4-[(Z)-AMINO(HYDROXYIMINO)METHYL]PIPERIDINE-1-CARBOXYLATE

HRID 2362660Notes

Reaction equation

HRID 2362660 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].[NH2:16][OH:17]>C(O)C>[OH:17]/[N:16]=[C:1](/[CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)\[NH2:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylate

Product 1

HCID 21937254TERT-BUTYL 4-[(Z)-AMINO(HYDROXYIMINO)METHYL]PIPERIDINE-1-CARBOXYLATE

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of tert-butyl 4-cyanopiperidine-1-carboxylate (0.5 g, 2.378 mmol) in ethanol (12 mL) was treated with hydroxylamine (50% in water, 0.51 mL, 8.32 mmol). The reaction was heated at 80° C. for 1.5 hours. The reaction was cooled to ambient temperature and concentrated under reduced pressure. The concentrate was dried to constant weight in a vacuum oven at 60° C. to provide the title compound. DCI(+) m/z 244.1 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe concentrate was dried to constant weight in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-8d4ac3ee3fd0461b9eaa10fb903c07b4
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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