Methanol → HCID 18377344, compound

HRID 2301098Notes

Reaction equation

HRID 2301098 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[C:10](=[CH:15]N(C)C)[CH2:9]1)=O)(C)(C)C.[OH2:19].[NH2:20][NH2:21].[CH3:22][OH:23]>>[C:10]([O:19][C:22]([N:20]1[C:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]=2[CH:15]=[N:21]1)=[O:23])([CH3:15])([CH3:11])[CH3:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Product 1

HCID 18377344HCID 18377344, compound

Procedure

N-t-Butoxycarbonyl-3-dimethylaminomethylene-4-piperidone (690 mg, 2.7 mmol) was dissolved in methanol (12 ml), and the solution was mixed with hydrazine monohydrate (160 mg, 3.3 mmol) and heated under reflux for 1 hour. The solvent was removed by evaporation from the reaction solution under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 400 mg (1.8 mmol, 66% in yield) of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. customThe solvent was removed by evaporation from the reaction solution under a reduced pressure
  4. customthe thus obtained material was separated
  5. custompurified by a silica gel column chromatography
  6. customto obtain

Sources & evidence

ORD record
ord-ae0d5bbfdbe14afa95c29ef655071a13
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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