Hydrochloric Acid → 1-Ethyl-4-[2-fluoro-3-(methylsulfonyl)phenyl]piperazine

HRID 2358070Notes

Reaction equation

HRID 2358070 reaction equation
[F:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:25][CH3:26].Cl>C(#N)C>[CH2:25]([N:15]1[CH2:16][CH2:17][N:12]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([S:8]([CH3:11])(=[O:9])=[O:10])[C:2]=2[F:1])[CH2:13][CH2:14]1)[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 574480501-[2-Fluoro-3-(methylsulfonyl)phenyl]piperazine

Product 1

HCID 574480301-Ethyl-4-[2-fluoro-3-(methylsulfonyl)phenyl]piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 1: 1-[2-fluoro-3-(methylsulfonyl)phenyl]piperazine (0.13 g, 0.52 mmol), acetonitrile (4 ml), potassium carbonate (0.14 g, 1.1 mmol) and iodoethane (0.48 ml, 0.52 mmol). Yield: 0.09 g (60%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 214-216° C. MS m/z (relative intensity, 70 eV) 286 (M+, 59), 272 (14), 271 (87), 201 (11), 57 (bp).

Workup

  1. customPreparation
  2. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-1f87dd0570894e64ade8933e78acaaba
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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