Acetic Acid → HCID 54133016, compound

HRID 614858Notes

Reaction equation

HRID 614858 reaction equation
[CH2:1]([C@@:3]1([CH:22](OCC)[O:23]CC)[CH2:8][CH2:7][CH2:6][N:5]([CH2:9][CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=3)[NH:13][CH:12]=2)[C:4]1=[O:21])[CH3:2].C(O)(=O)C.O>C(Cl)(Cl)Cl>[CH2:1]([C@@:3]1([CH:22]=[O:23])[CH2:8][CH2:7][CH2:6][N:5]([CH2:9][CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=3)[NH:13][CH:12]=2)[C:4]1=[O:21])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 54070147HCID 54070147, compound

Product 1

HCID 54133016HCID 54133016, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

39.05 g of (S)-3-ethyl-3-diethoxymethyl-1-[2-(5-fluoro-indol-3-yl)-ethyl]-2-piperidone are mixed with 80 cc of 99% acetic acid and 20 cc of water. The mixture is heated to the boil for half an hour in an atmosphere of nitrogen. After cooling, the solvent is removed by evaporation; the oily residue is subsequently taken up twice in 50 cc amounts of toluene and again concentrated by evaporation in order to remove most of the water and acetic acid. After crystallization from ethyl acetate/hexane (1:2) at 0°, brownish crystals are obtained. M.P. 116°, [α]D20 = -31.5° (1%, CHCl3).

Workup

  1. temperatureThe mixture is heated to the boil for half an hour in an atmosphere of nitrogen
  2. temperatureAfter cooling
  3. customthe solvent is removed by evaporation
  4. concentrationagain concentrated by evaporation in order
  5. customto remove most of the water and acetic acid
  6. customAfter crystallization from ethyl acetate/hexane (1:2) at 0°
  7. custombrownish crystals are obtained

Sources & evidence

ORD record
ord-76acd2352ddb4d8c88ab3b74635a0e1d
Source dataset
uspto-grants-1979_03
Patent number
US04146643

Reaction notes

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