Water → 7-[1-(Pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxamide oxime dihydrochloride

HRID 412519Notes

Reaction equation

HRID 412519 reaction equation
CS[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)=[CH:10][CH:11]=2)[CH2:6]1)=[NH:4].[ClH:29].[OH:30][NH2:31].C([O-])(=O)C.[Na+].O>C(O)C>[ClH:29].[ClH:29].[N:26]1[CH:27]=[CH:28][C:23]([N:20]2[CH2:21][CH2:22][CH:17]([CH2:16][O:15][C:9]3[CH:8]=[C:7]4[C:12]([CH2:13][CH2:14][N:5]([C:3](=[N:31][OH:30])[NH2:4])[CH2:6]4)=[CH:11][CH:10]=3)[CH2:18][CH2:19]2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 600641917-[1-(Pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carbothioimidic acid methyl ester

Product 1

HCID 865907237-[1-(Pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxamide oxime dihydrochlorideYield 53.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 7-[1-(pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carbothioimidic acid methyl ester (135 mg) in ethanol (3 ml) were added hydroxyamine hydrochloride (47 mg) and sodium acetate (56 mg), and the mixture was stirred at 40° C. for 2 hours. After completion of the reaction, water was added and the mixture was washed with chloroform. Thereto was added 4N aqueous sodium hydroxide solution, and the mixture was extracted with chloroform. The organic layer was washed successively with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained solid was treated with hydrogen chloride—ethanol solution and dried under reduced pressure to give the title compound (82 mg).

Workup

  1. additionwas added
  2. washthe mixture was washed with chloroform
  3. additionThereto was added 4N aqueous sodium hydroxide solution
  4. extractionthe mixture was extracted with chloroform
  5. washThe organic layer was washed successively with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. additionthe obtained solid was treated with hydrogen chloride—ethanol solution
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-3717f1f56fb646758527645694fa2841
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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