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

HRID 1709855Notes

Reaction equation

HRID 1709855 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.[H][H].[ClH:26].CCOCC>[Pt].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.CO>[OH2:16].[ClH:26].[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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 15020359alpha,alpha-Bis(4-fluorophenyl)-4-pyridineethanolHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

A mixture of 10.0 g (0.30 mole) α,α-bis(4-fluoropheny)-4-pyridineethanol of 1.2 g of 5% platinum on carbon catalyst in 200 ml of acetic and was shaken under an atomsphere 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 (72.4%)as a white, crystalline solid, m.p. 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 (72.4%)as a white, crystalline solid, m.p. 171°-173° C.

Sources & evidence

ORD record
ord-24d604a3540e401485aab46c83fd1feb
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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