Potassium Carbonate → HCID 21183785, compound

HRID 1384794Notes

Reaction equation

HRID 1384794 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:20]1([CH:26]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:27]2[CH2:30][CH:29](OS(C)(=O)=O)[CH2:28]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:29]2[CH2:30][N:27]([CH:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:28]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

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

Product 1

HCID 21183785HCID 21183785, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-tert-butoxycarbonylpiperazine (14.08 g), potassium carbonate (26.1 g), and 1-diphenylmethyl-3-methanesulphonyloxyazetidine (WO 96/05193) (20 g) in dry acetonitrile (600 mL) was heated under reflux for 32 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with water and brine. The organic phase was dried over sodium sulphate and evaporated to dryness in vacuo. The residue was purified by column chromatography over silica (dichloromethane/methanol 97/3 by volume) to afford the title compound as a solid (22.53 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 32 hours
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated to dryness in vacuo
  6. customThe residue was purified by column chromatography over silica (dichloromethane/methanol 97/3 by volume)

Sources & evidence

ORD record
ord-ccafc8a53a42491bb15ec11e08d15693
Source dataset
uspto-grants-2001_07
Patent number
US06262046B1

Reaction notes

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