Benzyl Bromide → 7-Bromo-2,3,4,5-tetrahydro-1H-1-benzazepine-9-carboxylic acid benzyl ester

HRID 4932Notes

Reaction equation

HRID 4932 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=[O:14])[C:5]2[NH:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH2:22]([O:14][C:13]([C:4]1[C:5]2[NH:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:12]=[C:2]([Br:1])[CH:3]=1)=[O:15])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 101992967-bromo-2,3,4,5-tetrahydro-1H-1-benzazepine-9-carboxylic acid

Product 1

HCID 536450037-Bromo-2,3,4,5-tetrahydro-1H-1-benzazepine-9-carboxylic acid benzyl esterYield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 7-bromo-2,3,4,5-tetrahydro-1H-1-benzazepine-9-carboxylic acid (8.53 g) dissolved in DMF (80 ml), were added potassium carbonate (13.8 g) and benzyl bromide (4.5 ml) and the mixture was stirred for 2 hours at room temperature. After the insoluble matter was filtered off and the filtrate was concentrated, a mixed liquid of ethyl acetate-benzene (1:1, 400 ml) was added to the residue, and the mixture was washed with water, dried over anhydrous sodium sulfate and then subjected to distilling off the solvent to give the intended compound 11.35 g (99.7%) as brown oily matter.

Workup

  1. filtrationAfter the insoluble matter was filtered off
  2. concentrationthe filtrate was concentrated
  3. additiona mixed liquid of ethyl acetate-benzene (1:1, 400 ml) was added to the residue
  4. washthe mixture was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationto distilling off the solvent

Sources & evidence

ORD record
ord-53267f682d9a4174af11e039aaa24acc
Source dataset
uspto-grants-1993_09
Patent number
US05242912

Reaction notes

Loading…