Hydrochloric Acid → 1-[2-(1,3-Dioxolan-2-YL)ethyl]-4-[2-fluoro-3-(methylsulfonyl)phenyl]-piperidine

HRID 2358057Notes

Reaction equation

HRID 2358057 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[CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH:27]1[O:31][CH2:30][CH2:29][O:28]1.Cl>C(#N)C>[O:28]1[CH2:29][CH2:30][O:31][CH:27]1[CH2:26][CH2:25][N:15]1[CH2:16][CH2:17][CH:12]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])[C:2]=2[F:1])[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 574480384-[2-Fluoro-3-(methylsulfonyl)phenyl]piperidine

Product 1

HCID 675324931-[2-(1,3-Dioxolan-2-YL)ethyl]-4-[2-fluoro-3-(methylsulfonyl)phenyl]-piperidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 1: 4-[2-fluoro-3-(methylsulfonyl)phenyl]piperidine (0.42 g, 1.63 mmol), acetonitrile (20 ml), potassium carbonate (0.45 g, 3.2 mmol) and 2-(2-bromoethyl)-1,3-dioxolan (0.205 ml, 1.65 mmol). Yield: 0.18 g (31%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 224-225° C. MS m/z (relative intensity, 70 eV) 357 (M+, 3), 270 (bp), 257 (59), 256 (27), 178 (90).

Workup

  1. customPreparation
  2. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-c8f71a5de3054dfb83c1491f87d7d681
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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