Hydrochloric Acid → Seridopidine

HRID 1887983Notes

Reaction equation

HRID 1887983 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=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][CH:12]([C:4]2[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=[C:2]([F:1])[CH:3]=2)[CH2:13][CH2:14]1)[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 57445555HCID 57445555, compound

Product 1

HCID 11572784Seridopidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 1: 4-[3-fluoro-5-(methylsulfonyl)phenyl]piperidine (0.4 g, 1.55 mmol), acetonitrile (5 ml), potassium carbonate (0.42 g, 3.0 mmol), 1-iodoethane (0.147 ml, 1.55 mmol). Yield: 0.28 g (63%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 176-178° C. MS m/z (relative intensity, 70 eV) 285 (M+, 15), 284 (16), 271 (16), 270 (bp), 84 (15).

Workup

  1. customPreparation
  2. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-2aa9e613586447468b063cbb9e32ba3b
Source dataset
uspto-grants-2013_08
Patent number
US08501777B2

Reaction notes

Loading…