Dichloromethane → 4-(3,5-Difluoro-2-(trifluoromethyl)phenyl)piperidine Hydrochloride

HRID 58436Notes

Reaction equation

HRID 58436 reaction equation
[F:1][C:2]1[C:3]([C:22]([F:25])([F:24])[F:23])=[C:4]([CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.C(Cl)[Cl:27]>Cl>[ClH:27].[F:1][C:2]1[C:3]([C:22]([F:25])([F:24])[F:23])=[C:4]([CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 118483534Tert-butyl 4-(3,5-difluoro-2-(trifluoromethyl)phenyl)piperidine-1-carboxylate

Product 1

HCID 1184833844-(3,5-Difluoro-2-(trifluoromethyl)phenyl)piperidine HydrochlorideYield 63%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl 4-(3,5-difluoro-2-(trifluoromethyl)phenyl)piperidine-1-carboxylate (27, 0.590 g, 1.61 mmol) in CH2Cl2 (10 mL) and HCl (2.0 N solution in Et2O, 10 mL) stirred at ambient temperature for 18 h. The resulting solids were filtered to afford 4-(3,5-difluoro-2-(trifluoromethyl)phenyl)piperidine hydrochloride (28) as a white solid (0.309 g, 63%). 1H NMR (300 MHz, CDCl3) δ 7.01-6.94 (m, 1H), 6.94-6.76 (m, 1H), 3.82-3.60 (m, 2H), 3.42-3.02 (m, 3H), 2.22-1.99 (m, 4H).

Workup

  1. filtrationThe resulting solids were filtered

Sources & evidence

ORD record
ord-1d1447a627f7452b83192e9db4519232
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

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