Sodium Bicarbonate → HCID 86588504, compound

HRID 584177Notes

Reaction equation

HRID 584177 reaction equation
[ClH:1].Cl.[F:3][C:4]([F:42])([F:41])[C:5]1[CH:6]=[C:7]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:12][C@H:11]1[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([CH3:33])[CH:27]=1)=[O:9].C(=O)(O)[O-].[Na+]>>[ClH:1].[ClH:1].[F:42][C:4]([F:3])([F:41])[C:5]1[CH:6]=[C:7]([CH:34]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:36]=1)[C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:12][C@H:11]1[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([CH3:33])[CH:27]=1)=[O:9]

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 86588505HCID 86588505, compound

Product 1

HCID 86588504HCID 86588504, compound

Procedure

(2R)-1-[3,5-Bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[3-(2-pyridyl)-2-propynyl]piperazine dihydrochloride (0.2 g) was made free with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated under reduced pressure. The resulting residue dissolved in methanol (10 ml) and the solution was hydrogenated over 10% palladium on activated carbon (50 mg) at room temperature under 2-3 atoms. After removal of catalyst by filtration, the filtrate was concentrated under reduced pressure. The residue was treated with 4N hydrogen chloride in ethyl acetate solution to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[3-(2-pyridyl)propyl]piperazine dihydrochloride.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. dissolutionThe resulting residue dissolved in methanol (10 ml)
  5. customwas hydrogenated over 10% palladium on activated carbon (50 mg) at room temperature under 2-3 atoms
  6. customAfter removal of catalyst
  7. filtrationby filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. additionThe residue was treated with 4N hydrogen chloride in ethyl acetate solution

Sources & evidence

ORD record
ord-90f324b6add5474d9e577fca2d6bed78
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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