Hydrazinecarboxaldehyde → HCID 178421605, compound

HRID 353117Notes

Reaction equation

HRID 353117 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21](OC)=[NH:22])[CH:16]=2)([CH3:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]([NH:27][NH2:28])=O>CO>[NH3:8].[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:14])([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[N:22]=[CH:25][NH:27][N:28]=3)[CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 22707876HCID 22707876, compound

Product 2

HCID 222AmmoniaHCID 178421605HCID 178421605, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of 1-benzyl-4-(3-(methoxycarbonimidoyl)phenyl)-4-methylpiperidine (Preparation 12, 735 mg, 2.28 mmol) in methanol (10 mL) was added a solution of formic acid hydrazide (274 mg, 4.56 mmol) in methanol (10 mL). The resultant mixture was stirred for 30 min and then concentrated in vacuo. The residual oil was heated at 100° C. for 1 h and then allowed to cool. This was purified on silica gel (50 g) by column chromatography eluting with a gradient of ethyl acetate:hexane:0.88 ammonia (80:20:1 to 90:10:1) to give the title compound as a clear oil (248 mg, 33%).

Workup

  1. concentrationconcentrated in vacuo
  2. temperatureto cool
  3. customThis was purified on silica gel (50 g) by column chromatography
  4. washeluting with a gradient of ethyl acetate

Sources & evidence

ORD record
ord-4c9e1ee05910455eb9706f155521dc7c
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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