Hydrochloric Acid → 4-[(4-Fluorophenyl)methyl]piperidine hydrochloride

HRID 970398Notes

Reaction equation

HRID 970398 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:22]>O1CCOCC1.CO.C(Cl)Cl.CCOC(C)=O.CO>[ClH:22].[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 226766794-(4-Fluoro-benzyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 170394924-[(4-Fluorophenyl)methyl]piperidine hydrochloride

Reagents, catalysts & solvents 3

HCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

N-(t-butoxycarbonyl)-4-(4-fluorophenylmethyl)piperidine (11.2 g, 38.2 mmol) was dissolved in 4M HCl in dioxane (50 mL). The reaction was stirred for 15 min and then conc. in vacuo to a white solid. The solid was dissolved in 3% MeOH/CH2Cl2 in EtOAc/MeOH while warming once all solids were dissolved hexanes was added. The crystallization was allowed to cool to room temperature and then placed at 4° C. for 16 h. The white solids were filtered off to yield 8.4 g of product. MS (ESI) 194 (M−HCl+H).

Workup

  1. temperaturewhile warming once all solids
  2. additionwas added
  3. customThe crystallization
  4. waitplaced at 4° C. for 16 h
  5. filtrationThe white solids were filtered off

Sources & evidence

ORD record
ord-62e93219c35e4a2dba44903b1a137026
Source dataset
uspto-grants-2007_12
Patent number
US07312222B2

Reaction notes

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