Water → HCID 9957151, compound

HRID 840165Notes

Reaction equation

HRID 840165 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:31]2[S:32][CH:33]=[C:34]([CH3:36])[CH:35]=2)=[C:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:20][CH:19]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:31]2[S:32][CH:33]=[C:34]([CH3:36])[CH:35]=2)=[C:25]2[CH2:30][CH2:29][N:28]([CH2:2][C:3]3[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=3)[C:6]([N:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)=[O:7])[CH2:27][CH2:26]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10014405148583-64-6HCID 110770424-[(4-Fluorophenyl)(4-methylthien-2-yl)methylene]piperidine

Product 1

HCID 9957151HCID 9957151, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of this benzoyl piperidine (2.3 9), the above 4-[(4-fluorophenyl)(4-methylthien-2-yl)methylene]piperidine (3 g) and triethylamine (3 ml) in toluene was boiled under reflux for 5 h. Water was added to the cooled mixture, the layers were separated and the toluene layer was separated, washed with brine, dried over sodium sulphate and evaporated. The resultant oil (5.6 g) was dissolved in dichloromethane and chromatographed on silica. Elution with dichloromethane/ammonium hydroxide (1%) containing increasing amounts of methanol gave fractions that on evaporation gave the title compound (4.36 g). A solution of this compound in ether was treated with with an ethereal solution of hydrogen chloride. The precipitate was collected and dried to give the hydrochloride salt (3.6 g) m.p. 118-142° C.

Workup

  1. temperatureunder reflux for 5 h
  2. customthe layers were separated
  3. customthe toluene layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. dissolutionThe resultant oil (5.6 g) was dissolved in dichloromethane
  8. customchromatographed on silica
  9. washElution with dichloromethane/ammonium hydroxide (1%)
  10. additioncontaining
  11. temperatureincreasing amounts of methanol
  12. customgave fractions that
  13. customon evaporation

Sources & evidence

ORD record
ord-527ef3e360ce434289e48d02115ab13a
Source dataset
uspto-grants-2002_04
Patent number
US06365604B1

Reaction notes

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