Ethyl bromoacetate → 3-bromo-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

HRID 745745Notes

Reaction equation

HRID 745745 reaction equation
[Br:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O>[Br:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:3]1=[O:13]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 27571843-Bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Product 1

HCID 133399633-bromo-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 20 g of 3-bromo-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine in 50 ml of dimethylformamide at 65° is added to a suspension of 114.7 g of potassium carbonate in 200 ml of dimethylformamide at room temperature maintaining the temperature of the reaction mixture below 30°. The reaction mixture is then stirred at room temperature for 90 minutes. A solution of 20.7 g of ethyl bromoacetate in 50 ml of dimethylformamide is added over a period of 30 minutes at room temperature. The reaction mixture is then stirred at 55° for one hour, filtered, the filter cake is washed with 100 ml of dimethylformamide, and the filtrate is evaporated to a small volume (removing about 200 ml of dimethylformamide) at 65° and 40 mm Hg. After cooling to 5°, 250 ml of water is added over a one hour period, maintaining the temperature below 10°, and the suspension is stirred at about 5° for 15 minutes. The solid is filtered off, washed with 200 ml of cyclohexane, and dried at 55° and 40-60 mm for 16 hours to give 3-bromo-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one.

Workup

  1. temperaturemaintaining the temperature of the reaction mixture below 30°
  2. stirringThe reaction mixture is then stirred at 55° for one hour
  3. filtrationfiltered
  4. washthe filter cake is washed with 100 ml of dimethylformamide
  5. customthe filtrate is evaporated to a small volume (removing about 200 ml of dimethylformamide) at 65°
  6. temperatureAfter cooling to 5°
  7. addition250 ml of water is added over a one hour period
  8. temperaturemaintaining the temperature below 10°
  9. stirringthe suspension is stirred at about 5° for 15 minutes
  10. filtrationThe solid is filtered off
  11. washwashed with 200 ml of cyclohexane
  12. customdried at 55°

Sources & evidence

ORD record
ord-72b24345efc047f494583bb164030045
Source dataset
uspto-grants-1986_07
Patent number
US04600534

Reaction notes

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