Ethanol → HCID 178485089, compound

HRID 412518Notes

Reaction equation

HRID 412518 reaction equation
C(O)C.CS[C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:19][CH:20]3[CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=4)[CH2:22][CH2:21]3)=[CH:13][CH:14]=2)[CH2:9]1)=[NH:7].[ClH:32].[CH3:33][NH2:34].C([O-])(=O)C.[Na+]>O>[ClH:32].[ClH:32].[CH3:33][NH:34][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:19][CH:20]3[CH2:21][CH2:22][N:23]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=4)[CH2:24][CH2:25]3)=[CH:13][CH:14]=2)[CH2:9]1)=[NH:7]

Participants

6

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 6364545Methylamine hydrochlorideHCID 600641917-[1-(Pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carbothioimidic acid methyl ester

Product 1

HCID 178485089HCID 178485089, compoundYield 119.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To an ethanol solution (2 ml) of 7-[1-(pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carbothioimidic acid methyl ester (100 mg) were added methylamine hydrochloride (20 mg) and sodium acetate (25 mg), and the mixture was stirred at 80° C. for 3 hours. After completion of the reaction, water was added and the mixture was washed with chloroform. Thereto was added aqueous sodium hydrogencarbonate solution and the mixture was washed with chloroform. To the aqueous layer was added 4N aqueous sodium hydroxide solution and the mixture was extracted with chloroform. The extract was washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated and the obtained residue was treated with hydrogen chloride—ethanol solution and dried under reduced pressure to give the title compound (80 mg).

Workup

  1. additionwas added
  2. washthe mixture was washed with chloroform
  3. additionThereto was added aqueous sodium hydrogencarbonate solution
  4. washthe mixture was washed with chloroform
  5. additionTo the aqueous layer was added 4N aqueous sodium hydroxide solution
  6. extractionthe mixture was extracted with chloroform
  7. washThe extract was washed successively with water and saturated brine
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. customthe solvent was evaporated
  10. additionthe obtained residue was treated with hydrogen chloride—ethanol solution
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-01eebf80c4f04420a8e549e52a75b185
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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