Ethanol → HCID 178444683, compound

HRID 353120Notes

Reaction equation

HRID 353120 reaction equation
[CH2:1]([N:7]1[CH2:12]C[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20](OC)=[NH:21])[CH:15]=2)([CH3:13])[CH:9](C)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH:25]([NH:27][NH2:28])=O.[CH2:29](O)[CH3:30]>CO>[NH3:7].[CH2:1]([N:7]1[CH2:8][CH2:9][C:10]([CH3:13])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:21]=[CH:25][NH:27][N:28]=3)[CH:15]=2)[CH:29]([CH3:30])[CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 702EthanolHCID 12229HydrazinecarboxaldehydeHCID 22707938HCID 22707938, compound

Product 2

HCID 222AmmoniaHCID 178444683HCID 178444683, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-hexyl-4-(3-(methoxycarbonimidoyl)phenyl)-3,4-dimethylpiperidine (Preparation 10, 200 mg, 0.35 mmol) in methanol (10 mL) was added a solution of formic acid hydrazide (30 mg, 0.5 mmol) in ethanol (20 mL). The resultant mixture was heated to reflux for 2 h and then concentrated in vacuo. The residual oil was heated at 100° C. for 20 minutes and then allowed to cool. The residue was purified by chromatography eluting with dichloromethane:methanol:0.88 ammonia (300:8:1) to give the title compound as a colourless oil (75 mg, 63%).

Workup

  1. temperatureto reflux for 2 h
  2. concentrationconcentrated in vacuo
  3. temperatureto cool
  4. customThe residue was purified by chromatography
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-9418e782f9a843198b5e2c05b0eb0c64
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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