Potassium Carbonate → tert-Butyl 4-(1,3-benzoxazol-2-yl)piperazine-1-carboxylate

HRID 33140

Reaction equation

HRID 33140 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[O:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119862-ChlorobenzoxazoleHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 40144297tert-Butyl 4-(1,3-benzoxazol-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 52.5 mmol 2-chlorobenzoxazol, 53.6 mmol piperazine-1-carboxylic acid tert-butyl ester and 63 mmol of potassium carbonate in 60 ml of acetonitrile was refluxed for 16 hours. The reaction mixture was concentrated, diluted with water and extracted with ethyl acetate. The organic phase was dried and concentrated to yield the title compounds as a slightly orange solid. MS (m/e): 304.2 (M+H+)

Workup

  1. temperaturewas refluxed for 16 hours
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f1df3f39742041a4a2e1e6310cf55b28
Source dataset
uspto-grants-2008_09
Patent number
US07429585B2

Linked notes

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