Hydrazine hydrate (1:1) → HCID 178444678, compound

HRID 353123Notes

Reaction equation

HRID 353123 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([C:13]2([CH3:26])[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:15][CH:14]2[CH3:25])[CH:10]=[CH:11][CH:12]=1)=O.O.[NH2:29]N>CO.O>[CH2:19]([N:16]1[CH2:17][CH2:18][C:13]([CH3:26])([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([C:5]3[CH:4]=[CH:3][NH:2][N:29]=3)[CH:8]=2)[CH:14]([CH3:25])[CH2:15]1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69835893HCID 69835893, compound

Product 1

HCID 178444678HCID 178444678, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-(3-(3-dimethylaminopropenoyl)phenyl)-1-hexyl-3,4-dimethylpiperidine (Preparation 38, 117 mg, 0.32 mmol) in a mixture of methanol (5.0 mL) and water (1.0 mL) was added hydrazine hydrate (0.1 mL, 3.2 mmol). The mixture was heated at reflux for 2 h and then cooled to room temperature. The mixture was concentrated in vacuo and saturated aqueous sodium hydrogencarbonate (10 mL) was added. The aqueous layer was extracted with dichloromethane (3×10 mL), the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate:hexane:0.88 ammonia (90:10:1). The title compound was isolated as clear oil (85 mg, 79%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationThe mixture was concentrated in vacuo and saturated aqueous sodium hydrogencarbonate (10 mL)
  4. additionwas added
  5. extractionThe aqueous layer was extracted with dichloromethane (3×10 mL)
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-995bccc60e294074b5da1fe54b215937
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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