Water → 3-chloro-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

HRID 482771Notes

Reaction equation

HRID 482771 reaction equation
[Cl: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].CC(C)([O-])C.[K+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].O>CN(C)C=O>[Cl: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

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 132434963-Chloro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 202447953-chloro-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 3-chloro-2,3,4,5-tetrahydro-1H-[1]benzazepine-2-one (1.95 g) in dimethylformamide (10 ml) was added dropwise with stirring to a solution of potassium t-butoxide (1.12 g) in dimethylformamide (10 ml) at 5°. The solution was stirred for an additional 15 minutes at 5°, then ethyl bromoacetate (1.78 g) in dimethylformamide (5 ml) was added dropwise. Stirring was continued for an additional 30 minutes at 5° and then for 3 hours at room temperature. The reaction mixture was cooled to 10° and water (100 ml) was added. The solution was extracted with chloroform (100 ml) and the chloroform solution washed with water (2×10 ml) and dried over sodium sulfate. The solvent was removed under reduced pressure to yield 3-chloro-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one; NMR(DMSO-d6): δ1.2(t,3H); 2.65(m,4H); 4.15(q,2H); 2.6 (d,2H); 7.3(m).

Workup

  1. stirringStirring
  2. waitwas continued for an additional 30 minutes at 5°
  3. waitfor 3 hours at room temperature
  4. temperatureThe reaction mixture was cooled to 10°
  5. extractionThe solution was extracted with chloroform (100 ml)
  6. washthe chloroform solution washed with water (2×10 ml)
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d19e1e086bdb4f0383193cc570c3c96d
Source dataset
uspto-grants-1986_03
Patent number
US04575503

Reaction notes

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