Potassium Carbonate → HCID 11529282, compound

HRID 2220074Notes

Reaction equation

HRID 2220074 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].C([O-])([O-])=O.[K+].[K+].I[CH2:24][CH2:25][CH3:26]>CC#N>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([N:11]2[CH2:16][CH2:15][N:14]([CH2:24][CH2:25][CH3:26])[CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 129889541-(3-(Methylsulfonyl)phenyl)piperazine

Product 1

HCID 11529282HCID 11529282, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1-(3-methanesulfonyl-phenyl)piperazine (350 mg) and ground K2CO3 (403 mg) was stirred in CH3CN (25 mL) at room temperature. 1-Iodo-propane (712 μL) was added. The mixture was refluxed overnight. The reaction mixture was filtered and the volatiles were evaporated in vacuum. The oily residue was chromatographed on a silica column with MeOH:CH2Cl2 (1:30 (v/v)) as eluent. Collection of the fractions containing pure product and evaporation of the solvent afforded pure 1-(3-methanesulfonyl-phenyl)-4-propyl-piperazine (220 mg). The amine was converted into the HCl salt and recrystallized from ethanol/diethylether: m.p. 233° C. MS m/z (relative intensity, 70 eV) 282 (M+, 30), 254 (15), 253 (bp), 210 (17), 70 (21).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe volatiles were evaporated in vacuum
  4. customThe oily residue was chromatographed on a silica column with MeOH:CH2Cl2 (1:30 (v/v)) as eluent
  5. customCollection of the fractions
  6. additioncontaining pure
  7. customproduct and evaporation of the solvent

Sources & evidence

ORD record
ord-0522313bfe6844e4b80a436849c9a786
Source dataset
uspto-grants-2008_08
Patent number
US07417043B2

Reaction notes

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