Hydrochloric Acid → 1-Ethyl-4-{2-fluoro-3-[(trifluoromethyl)sulfonyl]phenyl}piperidine

HRID 1878978Notes

Reaction equation

HRID 1878978 reaction equation
[F:1][C:2]1[C:7]([S:8]([C:11]([F:14])([F:13])[F:12])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:28][CH3:29].Cl>C(#N)C>[CH2:28]([N:18]1[CH2:19][CH2:20][CH:15]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([S:8]([C:11]([F:14])([F:13])[F:12])(=[O:9])=[O:10])[C:2]=2[F:1])[CH2:16][CH2:17]1)[CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 574480514-{2-Fluoro-3-[(trifluoromethyl)sulfonyl]phenyl}piperidine

Product 1

HCID 117028411-Ethyl-4-{2-fluoro-3-[(trifluoromethyl)sulfonyl]phenyl}piperidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 1: 4-{2-fluoro-3-[(trifluoromethyl)sulfonyl]phenyl}-piperidine (0.11 g, 0.35 mmol), acetonitrile (4 ml), potassium carbonate (0.063 g, 0.7 mmol) and 1-iodoethane (0.055 g, 0.35 mmol). Yield: 0.068 g (57%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 189-191° C. MS m/z (relative intensity, 70 eV) 339 (M+, 8), 325 (15), 324 (bp), 205 (6), 191 (15).

Workup

  1. customPreparation
  2. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-619a7895794b4bd18be5dcbee3c73bd4
Source dataset
uspto-grants-2012_11
Patent number
US08314126B2

Reaction notes

Loading…