tert-Butylhydrazine monohydrochloride → HCID 57337174, compound

HRID 2403649Notes

Reaction equation

HRID 2403649 reaction equation
O=[C:2]1[CH2:22][CH2:21][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:7][CH2:6]2)[CH:4]=[CH:3]1.[ClH:23].[C:24]([NH:28][NH2:29])([CH3:27])([CH3:26])[CH3:25]>C(O)C>[ClH:23].[C:24]([NH:28]/[N:29]=[C:2]1/[CH:3]=[CH:4][C:5]2([CH2:21][CH2:22]/1)[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:7][CH2:6]2)([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 81889tert-Butylhydrazine monohydrochlorideHCID 23435732Benzyl 9-oxo-3-azaspiro(5.5)undec-7-ene-3-carboxylate

Product 1

HCID 57337174HCID 57337174, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Benzyl 9-oxo-3-azaspiro[5.5]undec-7-ene-3-carboxylate (4.89 g, 16.3 mmol) was dissolved in ethanol (60 mL) and tert-butylhydrazine hydrochloride (2.44 g, 19.6 mmol) was added. The mixture was heated at reflux for 4 hours and then stirred at 60° C. for 48 hours. The reaction was cooled to room temperature and concentrated under reduced pressure to give a tan oil which solidified upon standing to yield 6.60 g (99%) of the title compound as a tan solid. +ESI (M+H) 370.3; 1H NMR (400 MHz, CDCl3, δ): 7.26-7.42 (m, 5 H), 6.46 (d, J=10.0 Hz, 1 H), 6.26 (br. s., 1 H), 5.08-5.16 (m, 2 H), 3.43-3.58 (m, 4 H), 3.19 (s, 2 H), 1.78 (s, 2 H), 1.44-1.63 (m, 4 H), 1.17-1.30 (m, 9 H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe reaction was cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. customto give a tan oil which

Sources & evidence

ORD record
ord-a0c112b77ecb4526888b0e5f19c8179a
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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