Potassium Carbonate → HCID 16123291, compound

HRID 2063309Notes

Reaction equation

HRID 2063309 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[C:30](Cl)(=[O:33])[CH2:31][CH3:32]>C(#N)C>[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH:10]([N:12]3[CH2:17][CH2:16][N:15]([C:30](=[O:33])[CH2:31][CH3:32])[CH2:14][CH2:13]3)[CH2:11]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 62324Propionyl chlorideHCID 16123292HCID 16123292, compound

Product 1

HCID 16123291HCID 16123291, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-[1-(diphenylmethyl)azetidin-3-yl]piperazine (250 mg, 0.81 mmol), K2CO3 (146 mg, 1.1 mmol), propionyl chloride (98 mg, 1.1 mmol) and acetonitrile (6 mL) was stirred at RT for 16 h. The mixture was filtered through a phase separator column and the solvent was removed by evaporation. The residue was dissolved in methylene chloride and the solution washed with aqueous NaHCO3. The organic phase was separated by using a phase separator column and then the solvent was removed by evaporation. There was obtained 216 mg (73%) of 1-[1-(diphenylmethyl)azetidin-3-yl]-4-propionylpiperazine as an oil. 1H NMR (500 MHz, CDCl3): 1.1-1.2 (t, 3H), 2.2-2.4 (m, 6H), 2.9 (t, 2H), 3.0 (m, 1H), 3.4-3.5 (m, 4H), 3.6 (b, 2H), 4.4 (s, 1H), 7.2 (m, 2H), 7.3 (m, 4H), 7.4 (m, 4H); LCMS: m/z 364 (M+1)+.

Workup

  1. filtrationThe mixture was filtered through a phase separator column
  2. customthe solvent was removed by evaporation
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washthe solution washed with aqueous NaHCO3
  5. customThe organic phase was separated
  6. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-700a77b4f085497ebaf1a0559600f645
Source dataset
uspto-grants-2012_10
Patent number
US08288370B2

Reaction notes

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