Methylamine → HCID 15839873, compound

HRID 1377484Notes

Reaction equation

HRID 1377484 reaction equation
[CH3:1][NH2:2].[CH3:3][N:4]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:12]([CH2:20][CH2:21][C:22](OC)=[O:23])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:26]>ClCCl.CO>[CH3:1][NH:2][C:22](=[O:23])[CH2:21][CH2:20][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:26])[N:4]([CH3:3])[C:13]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 15839871HCID 15839871, compound

Product 1

HCID 15839873HCID 15839873, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A stream of gaseous methylamine is passed into a 250 ml round-bottomed flask containing a solution of 1.25 g (3.85 mmol) of methyl 2-methyl-1-oxo-3-phenyl-1,2-dihydroisoquinoline-4-propanoate in 20 ml of dichloromethane and 80 ml of methanol until saturation and the mixture is left stirring at room temperature for 3 days. The solvents are evaporated under reduced pressure and the residue is purified by chromatography on a column of silica gel, elution being carried out with a mixture of dichloromethane and ethyl acetate ranging from 100/0 to 80/20 and then with a 95/5 mixture of dichloromethane and methanol. After recrystallizing from acetonitrile, 0.85 g (2.65 mmol) of white crystalline solid is obtained. Melting point: 185°-186° C.

Workup

  1. waitthe mixture is left
  2. customThe solvents are evaporated under reduced pressure
  3. customthe residue is purified by chromatography on a column of silica gel, elution
  4. additionbeing carried out with a mixture of dichloromethane and ethyl acetate ranging from 100/0 to 80/20
  5. additionwith a 95/5 mixture of dichloromethane and methanol
  6. customAfter recrystallizing from acetonitrile

Sources & evidence

ORD record
ord-260b2760f58349429ae29974e88bc955
Source dataset
uspto-grants-1997_09
Patent number
US05665733

Reaction notes

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