Hydrochloric Acid → 4-[2,2-Bis(4-fluorophenyl)ethyl]piperidine hydrochloride hydrate

HRID 1460246Notes

Reaction equation

HRID 1460246 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([OH:16])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[ClH:24].CCOCC>[Pt].C(O)(=O)C.CO>[OH2:16].[ClH:24].[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 15020359alpha,alpha-Bis(4-fluorophenyl)-4-pyridineethanol

Product 1

HCID 199831054-[2,2-Bis(4-fluorophenyl)ethyl]piperidine hydrochloride hydrate

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 10.0 g (0.3 mole) α,α-bis(4-fluoropheny)-4-pyridineethanol and 1.2 g of 5% platinum on carbon catalyst in 200 ml of acetic acid was shaken under an atmosphere of hydrogen (49 psi) for 16 hr. The solution was filtered through Celite®, and the solvent was removed in vacuo. The residue was partitioned between methylene chloride and dilute sodium hydroxide. The solvent was removed in vacuo to give an oil. This was dissolved in methanol, an excess of ethereal hydrogen chloride was added and ether was added. A precipitate was collected to give 7.58 g (72%) as a white crystalline solid, mp 171°-173° C.

Workup

  1. filtrationThe solution was filtered through Celite®
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between methylene chloride and dilute sodium hydroxide
  4. customThe solvent was removed in vacuo
  5. customto give an oil
  6. customA precipitate was collected
  7. customto give 7.58 g (72%) as a white crystalline solid, mp 171°-173° C.

Sources & evidence

ORD record
ord-c08aac4669554e6592afbd35ae73ff0d
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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