Hydrochloric Acid → 4-(2-Chloro-3-fluorophenyl)piperidine Hydrochloride

HRID 58424Notes

Reaction equation

HRID 58424 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=2[Cl:21])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.CCOCC>[ClH:21].[Cl:21][C:15]1[C:16]([F:20])=[CH:17][CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118483383Tert-butyl-4-(2-chloro-3-fluorophenyl)piperidine-1 carboxylate

Product 1

HCID 1184834264-(2-Chloro-3-fluorophenyl)piperidine HydrochlorideYield 148.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-chloro-3-fluorophenyl) piperidine-1-carboxylate (13, 0.520 g, 1.66 mmol) in CH2Cl2 (10 mL) under an atmosphere of N2 was added HCl (2 N in Et2O, 10 mL) solution was stirred at ambient temperature for 18 h. The reaction mixture was diluted with Et2O (20 mL). The resulting precipitate was collected by filtration and washed with Et2O to provide 4-(2-chloro-3-fluorophenyl)piperidine hydrochloride (14) as a white solid (309 mg, 74%): 1H NMR (300 MHz, DMSO-d6) δ 8.81-8.55 (m, 2H), 7.47-7.37 (m, 1H), 7.36-7.27 (m, 1H), 7.21-7.13 (m, 1H), 3.43-3.20, (m, 3H), 3.17-2.97 (m, 2H), 2.00-1.73 (m, 4H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with Et2O

Sources & evidence

ORD record
ord-e782cf3193fb484fa0d4a27fdf0d6389
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

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