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Dimethylformamide → 1-[gamma-(p-Chlorophenylsulfinyl)-propyl]piperidine hydrochloride

HRID 1657432
Notes
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Reaction equation

HRID 1657432 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:10][CH2:11][CH2:12]Cl)=[O:9])=[CH:4][CH:3]=1.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O.C1C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:10][CH2:11][CH2:12][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:9])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8082PiperidineHCID 10340Sodium CarbonateHCID 197720711-(p-Chlorophenylsulfinyl)-3-chloropropane

Product 1

HCID 215334301-[gamma-(p-Chlorophenylsulfinyl)-propyl]piperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 241
Benzene
Solvent
HCID 962WaterSolvent

Procedure

A mixture of 2.46 g. of 1-(p-chlorophenylsulfinyl)-3-chloropropane, 0.9 g. of piperidine, 0.53 g. of sodium carbonate in 30 ml. of dimethylformamide is heated for 3 hours at a temperature of 80° - 87°C. After the reaction mixture has been cooled, a mixture of benzene and water is added thereto. The aqueous layer is separated and extracted with benzene. The organic layers are combined, washed with water, dried over sodium sulfate and evaporated under reduced pressure. The oily residue is dissolved in ether and treated with ethanolic hydrogen chloride under cooling. The precipitate is collected by filtration and dried to give 1-[γ-(p-chlorophenylsulfinyl)-propyl]piperidine hydrochloride, m.p.: 170° - 174°C. Recrystallization from benzene gives white crystals, m.p.: 176° - 177°C.

Workup

  1. additionA mixture of 2.46 g
  2. temperatureAfter the reaction mixture has been cooled
  3. additionis added
  4. customThe aqueous layer is separated
  5. extractionextracted with benzene
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure
  9. dissolutionThe oily residue is dissolved in ether
  10. additiontreated with ethanolic hydrogen chloride
  11. temperatureunder cooling
  12. filtrationThe precipitate is collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-f5ed92738bf044d4bd62b763fa3aba78
Source dataset
uspto-grants-1976_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03960873

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes