Sodium Carbonate → HCID 140401478, compound

HRID 613257Notes

Reaction equation

HRID 613257 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl.[NH2:8][OH:9].O=[C:11]([C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)=[CH:19][CH:18]=1)[CH2:12][CH2:13][C:14]([OH:16])=[O:15]>O.C(O)C>[OH:9]/[N:8]=[C:11](\[C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)=[CH:19][CH:18]=1)/[CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 15463122HCID 15463122, compound

Product 1

HCID 140401478HCID 140401478, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium carbonate (0.80 g, 5.76 mmol) was added to hydroxylamine hydrochloride (0.80 g, 11.5 mmol) in water (3 mL), and the mixture stirred for 15 minutes with ice cooling. The resulting mixture was added to 4-oxo-4-[4-(4-phenyl-piperidin-1-yl)-phenyl]-butyric acid (2.99 g, 8.86 mmol) (Example 1) in ethanol (50 mL) and the resulting mixture refluxed for 6 hours, concentrated to one-third volume, and allowed to cool. The resulting precipitate was dissolved in hot sodium bicarbonate solution, filtered, and the filtrate acidified with 1M HCl to yield a slurry which was filtered, washed with water, and dried in vacuo to give the title compound as a white solid (1.17 g, %C,H,N found: 71.77, 6.79, 7.88).

Workup

  1. temperaturethe resulting mixture refluxed for 6 hours
  2. concentrationconcentrated to one-third volume
  3. temperatureto cool
  4. dissolutionThe resulting precipitate was dissolved in hot sodium bicarbonate solution
  5. filtrationfiltered
  6. customto yield a slurry which
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a350e61bd1d34c4e8a38d556b706e83e
Source dataset
uspto-grants-1999_12
Patent number
US06008220

Reaction notes

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