Ethyl bromoacetate → 3-(10,11-Dihydro-5h-dibenz[b,f]azepin-5-ylmethyl)-1-piperidylacetic acid ethyl ester

HRID 323697Notes

Reaction equation

HRID 323697 reaction equation
O.C(O)(=O)C(O)=O.[CH:8]1[C:18]2[CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[N:13]([C:23]([CH:25]3[CH2:30][CH2:29][CH2:28][N:27](CC4C=CC=CC=4)[CH2:26]3)=O)[C:12]=2[CH:11]=[CH:10][CH:9]=1.C1C2CCC3C=CC=CC=3N(C(C3CCCN(CC4C=CC=CC=4)C3)=O)C=2C=CC=1.C(O)(=O)C(O)=O.Br[CH2:75][C:76]([O:78][CH2:79][CH3:80])=[O:77].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:79]([O:78][C:76](=[O:77])[CH2:75][N:27]1[CH2:28][CH2:29][CH2:30][CH:25]([CH2:23][N:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:18]=3[CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]2=3)[CH2:26]1)[CH3:80]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1317224903-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylcarbonyl)-1-benzylpiperidine hydrogen oxalate hemihydrate

Product 1

HCID 538348943-(10,11-Dihydro-5h-dibenz[b,f]azepin-5-ylmethyl)-1-piperidylacetic acid ethyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the above piperidine (2.05 g, 7 mmol), ethyl bromoacetate (1.36 g, 8.1 mmol), potassium carbonate (1.7 g, 12.3 mmol) and acetone (50 ml) was heated at reflux temperature under stirring for 7 h. The mixture was filtered and the solvent evaporated in vacuo. The oily residue was purified on silica gel (20 g) using ethyl acetate as eluent to give 2.3 g (87%) 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)-1-piperidylacetic acid ethyl ester as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature
  3. filtrationThe mixture was filtered
  4. customthe solvent evaporated in vacuo
  5. customThe oily residue was purified on silica gel (20 g)

Sources & evidence

ORD record
ord-5205845a8cd64092b676e2771e162424
Source dataset
uspto-grants-2001_04
Patent number
US06214816B1

Reaction notes

Loading…