Hydrazine → 5-Benzyl-5-azaspiro[2.4]heptane

HRID 1010800Notes

Reaction equation

HRID 1010800 reaction equation
[CH2:1]([N:8]1[CH2:14][C:13](=O)[C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.[OH-].[Na+]>O>[CH2:1]([N:8]1[CH2:14][CH2:13][C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 14798Sodium HydroxideHCID 103527905-Benzyl-5-azaspiro[2.4]heptan-7-one

Product 1

HCID 584529275-Benzyl-5-azaspiro[2.4]heptane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-benzyl-5-azaspiro[2.4]heptan-7-one (300 mg) was mixed with hydrazine (600 mg) and NaOH (300 mg) in H2O (2 ml). The mixture was refluxed for overnight and purified by column chromatography to give 5-benzyl-5-azaspiro[2.4]heptane that was hydrogenated at 50 psi with Pd—C (10%, 80 mg) in EtOH (15 ml) for overnight followed by filtration through Celite to give 5-azaspiro[2.4]heptane. This product was mixed with 2-Bromoethanol and K2CO3 in Acetonitrile. The reaction was refluxed overnight and filtered, the filtrate was evaporated and purified on silica gel column to give the titled product. Mass: (M+1), 142

Workup

  1. temperatureThe mixture was refluxed for overnight
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-68ab05b813394d79933fe37d6bd4629e
Source dataset
uspto-grants-2011_07
Patent number
US07977346B2

Reaction notes

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