Colchicine → N-methylcolchiceinamide

HRID 1379911Notes

Reaction equation

HRID 1379911 reaction equation
[CH3:1][C:2]([NH:4][C@@H:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17](OC)[C:18]([CH:20]=2)=[O:19])[C:13]2[C:12]([O:24][CH3:25])=[C:11]([O:26][CH3:27])[C:10]([O:28][CH3:29])=[CH:9][C:8]=2[CH2:7][CH2:6]1)=[O:3].[CH3:30][NH2:31]>C(O)C>[CH3:1][C:2]([NH:4][CH:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([NH:31][CH3:30])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:8](=[CH:9][C:10]([O:28][CH3:29])=[C:11]([O:26][CH3:27])[C:12]=2[O:24][CH3:25])[CH2:7][CH2:6]1)=[O:3]

Participants

4

Reactant 2

HCID 6167ColchicineHCID 6329Methylamine

Product 1

HCID 45314N-methylcolchiceinamideYield 84.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixed solution of colchicine (5.00 g, 12.5 mmoles), an aqueous 40% methylamine solution (10 ml, 130 mmol) and ethyl alcohol (10 ml) was subjected to reaction at 120° C. for 20 hours under stirring in a sealed tube. The solvent was distilled off, water (10 ml) was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was separated, washed with water and dried. The solvent was evaporated, and the residue was separated and purified by silica gel column chromatography [chloroform: methanol (20:1)]. Thereby, 4.20 g of N-methylcolchiceinamide was obtained as yellow crystals (yield 84%). ##STR13##

Workup

  1. distillationThe solvent was distilled off
  2. additionwater (10 ml) was added to the residue
  3. extractionthe mixture was extracted with chloroform
  4. customThe chloroform layer was separated
  5. washwashed with water
  6. customdried
  7. customThe solvent was evaporated
  8. customthe residue was separated
  9. custompurified by silica gel column chromatography [chloroform: methanol (20:1)]

Sources & evidence

ORD record
ord-69dc62c6376742d1adb63e0181442671
Source dataset
uspto-grants-1997_09
Patent number
US05672757

Reaction notes

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