Ethanolamine → HCID 68534498, compound

HRID 1436910Notes

Reaction equation

HRID 1436910 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH:12]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](N1C=CN=C1)([N:27]1[CH:31]=[CH:30]N=C1)=[O:26].C(CN)[OH:38]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:25]([NH:27][CH2:31][CH2:30][OH:38])=[O:26])[CH2:13][CH:12]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 682631,1'-CarbonyldiimidazoleHCID 68534638HCID 68534638, compound

Product 1

HCID 68534498HCID 68534498, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

In 21 ml of toluene was dissolved 1.63 g of 1-benzyloxycarbonyl-4-hydroxy-2-(2-methylphenyl)piperidine, added thereto was 973 mg of 1,1′-carbonyldiimidazole, and the mixture was stirred at 60° C. for an hour. To the solution was added 1.21 ml of ethanolamine, and the mixture was stirred at 60° C. for 6 hours. To the reaction mixture was added distilled water, and extracted with chloroform. The organic layer was dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:acetone=9:1→chloroform:methanol=19:1), to give 1.34 g of 1-benzyloxycarbonyl-4-(2-hydroxyethylaminocarbonyloxy)-2-(2-methylphenyl)piperidine.

Workup

  1. additionadded
  2. stirringthe mixture was stirred at 60° C. for 6 hours
  3. additionTo the reaction mixture was added
  4. distillationdistilled water
  5. extractionextracted with chloroform
  6. customThe organic layer was dried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:acetone=9:1→chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-f21f667aca2949f79334b36bc3a049bc
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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