Tetrabenazine → HCID 12087400, compound

HRID 1774307

Reaction equation

HRID 1774307 reaction equation
[CH3:1][CH:2]([CH2:4][CH:5]1[C:18](=O)[CH2:17][CH:16]2[N:7]([CH2:8][CH2:9][C:10]3[C:15]2=[CH:14][C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=3)[CH2:6]1)[CH3:3].C(O)(=O)C.[NH3:28].[BH4-].[Na+]>CO>[CH2:4]([CH:5]1[CH2:6][N:7]2[CH2:8][CH2:9][C:10]3[C:15]([CH:16]2[CH2:17][CH:18]1[NH2:28])=[CH:14][C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=3)[CH:2]([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 6018TetrabenazineHCID 12432Ammonia acetateHCID 4311764Sodium borohydride

Product 1

HCID 12087400HCID 12087400, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

With reference to FIG. 11, tetrabenazine (317 mg, 1 mmol) was dissolved in methanol (MeOH, 10 ml) and cooled with ice-water. To this solution, ammonia acetate (500 mg) was added, followed by the addition of sodium borohydride (50 mg) in portion. The reaction was stirred at room temperature for 24 hours and quenched with water. The aqueous solution was extracted with methylene chloride (10 ml) twice. The combined organic phase was washed with brine and dried with sodium sulfate. After removing the solvent, the residue was purified by chromatography. One hundred and fifty milligrams of (HG-6) (3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-amine) was obtained as white solid (yield: 47%).

Workup

  1. customquenched with water
  2. extractionThe aqueous solution was extracted with methylene chloride (10 ml) twice
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried with sodium sulfate
  5. customAfter removing the solvent
  6. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-52ff39c7cb9248df890d10e599795211
Source dataset
uspto-grants-2016_02
Patent number
US09260391B2

Linked notes

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