Potassium Carbonate → HCID 21183785, compound

HRID 1788349Notes

Reaction equation

HRID 1788349 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N:7]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.CS(O[CH:25]1[CH2:28][N:27]([CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:26]1)(=O)=O>C(#N)C.O1CCCC1>[C:30]1([CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:27]2[CH2:28][CH:25]([N:10]3[CH2:11][CH2:12][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:9]3)[CH2:26]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 21183785HCID 21183785, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (26 g) was added to a solution of tert-butyl piperazine-1-carboxylate (7.7 g) in acetonitrile (100 ML), to which a suspension of 1-(diphenylmethyl)azetidin-3-yl methanesulfonate (12.05 g) in tetrahydrofuran (30 mL) was added at room temperature, and the mixture was stirred for 4 hours at 100° C., and then concentrated. To the resulting residue was added water, and the mixture was extracted with ethyl acetate twice. The extract was dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to column chromatography on silica gel (hexane:ethyl acetate=3:1→1:2), and the product was washed with tert-butyl methyl ether and collected by filtration to give the title compound (10.68 g) having the following physical data.

Workup

  1. additionwas added at room temperature
  2. concentrationconcentrated
  3. additionTo the resulting residue was added water
  4. extractionthe mixture was extracted with ethyl acetate twice
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. washthe product was washed with tert-butyl methyl ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-b49d4e785e224d17b74cff95d54c54be
Source dataset
uspto-grants-2009_03
Patent number
US07511159B2

Reaction notes

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