Ethanolamine → n-Tert-butoxycarbonyl-4-[4-(4,5-dihydrooxazol-2-yl)phenyl]piperazine

HRID 1356986Notes

Reaction equation

HRID 1356986 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].OCC(CO)O.C(=O)([O-])[O-].[K+].[K+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]#N)=[CH:32][CH:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(O)CO>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[O:2][CH2:1][CH2:3][N:4]=3)=[CH:32][CH:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 753GlycerolHCID 11430Potassium CarbonateHCID 2795512Tert-butyl 4-(4-cyanophenyl)piperazine-1-carboxylate

Product 1

HCID 18504842n-Tert-butoxycarbonyl-4-[4-(4,5-dihydrooxazol-2-yl)phenyl]piperazineYield 37.1%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of ethanolamine (0.91 ml; 15.0 mmol), glycerol (2.7 g), ethylene glycol (5.6 g) and potassium carbonate (2.1 g; 15.0 mmol) is heated at 105° C. for 30 min. The intermediate 1A (2.3 g; 8.04 mmol) is then added and the mixture is heated for 5 days at 105° C. The precipitate formed is filtered on sintered glass and washed with water and with petroleum ether to give compound 5A (988 mg; 37%) in the form of a beige solid.

Workup

  1. temperaturethe mixture is heated for 5 days at 105° C
  2. customThe precipitate formed
  3. filtrationis filtered on sintered glass
  4. washwashed with water and with petroleum ether

Sources & evidence

ORD record
ord-093fa707e13c4c61936a263f5ea8f5d2
Source dataset
uspto-grants-2003_07
Patent number
US06589953B2

Reaction notes

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