Sulfuric Acid → HCID 19883507, compound

HRID 345583Notes

Reaction equation

HRID 345583 reaction equation
Cl.Cl.[CH2:3]([N:5]([CH2:30][CH3:31])[CH2:6][CH2:7][O:8][CH:9]1[C:14](OC)([O:15]C)[CH2:13][CH2:12][N:11]([CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:10]1)[CH3:4].S(=O)(=O)(O)O>O>[CH2:30]([N:5]([CH2:3][CH3:4])[CH2:6][CH2:7][O:8][CH:9]1[C:14](=[O:15])[CH2:13][CH2:12][N:11]([CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:10]1)[CH3:31]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 19883498HCID 19883498, compound

Product 1

HCID 19883507HCID 19883507, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.07 parts of N,N-diethyl-2-[[1-[3-(4-fluorophenoxy)propyl]-4,4-dimethoxy-3-piperidinyl]-oxy]ethanamine dihydrochloride, 7.36 parts of a sulfuric acid solution 96% and 500 parts of water was stirred and refluxed for 17 hours. The reaction mixture was allowed to cool and washed with 2,2'-oxybispropane. The aqueous phase was separated and alkalized with sodium carbonate. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated, yielding 8.0 parts (75%) of 3-[2-(diethylamino)ethoxy]-1-[3-(4-fluorophenoxy)propyl]-4-piperidinone as a residue (intermediate 120).

Workup

  1. temperaturerefluxed for 17 hours
  2. temperatureto cool
  3. washwashed with 2,2'-oxybispropane
  4. customThe aqueous phase was separated
  5. extractionThe product was extracted with dichloromethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (95:5 by volume) saturated with ammonia
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated

Sources & evidence

ORD record
ord-583a55981eee4e5f96d3028eeef926f0
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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