tert-Butyl carbazate → Tert-butyl 4-[(tert-butoxycarbonyl)hydrazono]piperidine-1-carboxylate

HRID 1931582Notes

Reaction equation

HRID 1931582 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[NH:16][NH2:17]>>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][C:11](=[N:17][NH:16][C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

3

Reactant 2

HCID 70091tert-Butyl carbazateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 20824233Tert-butyl 4-[(tert-butoxycarbonyl)hydrazono]piperidine-1-carboxylateYield 94.3%

Procedure

To a three-neck flask equipped with a mechanical stirrer and a condenser was loaded 1-Boc-4-piperidone (10.0 g, 50.2 mmol), tert-butyl carbazate (7.30 g, 55.2 mmol) and hexanes (20 mL). The mixture was heated to reflux for 3 h, then cooled to room temperature and filtered. The solid was washed with hexanes and dried at room temperature to give 4-(tert-butoxycarbonyl-hydrazono)piperidine-1-carboxylic acid tert-butyl ester (14.84 g, 94%) as a white powder. 1H NMR (CDCl3) δ 1.46 (s, 9H), 1.50 (s, 9H), 2.32 (m, 2H), 2.52 (m, 2H), 3.55 (m, 4H), 7.48 (br, 1H).

Workup

  1. customTo a three-neck flask equipped with a mechanical stirrer and a condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 3 h
  4. filtrationfiltered
  5. washThe solid was washed with hexanes
  6. customdried at room temperature

Sources & evidence

ORD record
ord-613be7598a9d47ed9c0cf7e68ede2574
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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