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Hydrochloric Acid → 1-Benzyl-4-(p-trifluoromethylphenoxy)piperidine hydrochloride

HRID 437574
Notes
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Reaction equation

HRID 437574 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].F[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1.[ClH:30]>C(O)(C)C.CN(C)C=O>[ClH:30].[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-HCID 784611-Benzylpiperidin-4-olHCID 178418361HCID 178418361, compound

Product 1

HCID 202630171-Benzyl-4-(p-trifluoromethylphenoxy)piperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 40.0 g of 1-benzyl-4-piperidinol in 75 ml. of dimethylformamide is added slowly to a stirred suspension of 6.7 g of a 50% oil dispersion of sodium hydride in 300 ml. of dimethylformamide at 60°-70° C. After addition is complete, heating is continued until no more hydrogen gas is liberated. A solution of 39.5 g of 1-fluoro-4-trifluoromethylbenzene in 50 ml. of dimethylformamide is added slowly while maintaining the reaction temperature at 60°-70° C. After addition is complete, stirring and heating at 70°-75° C. is continued for 16 hours. The mixture is poured into 1 l. of water and extracted with benzene. The combined benzene extracts are washed with water, dried, and solvent is removed under reduced pressure, leaving an oil. The oil is taken up in isopropanol and treated with ethereal-HCl, giving a white solid of 1-benzyl-4-(p-trifluoromethylphenoxy)piperidine hydrochloride.

Workup

  1. customat 60°-70° C
  2. additionAfter addition
  3. temperatureheating
  4. temperaturewhile maintaining the reaction temperature at 60°-70° C
  5. additionAfter addition
  6. temperatureheating at 70°-75° C.
  7. additionThe mixture is poured into 1 l
  8. extractionof water and extracted with benzene
  9. washThe combined benzene extracts are washed with water
  10. customdried
  11. customsolvent is removed under reduced pressure
  12. customleaving an oil

Sources & evidence

ORD record
ord-f26bef372c3e4341bd1766ceb86a3f7a
Source dataset
uspto-grants-1977_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04031221

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes