Potassium Carbonate → 1-(5-Chloropentanoyl)-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one

HRID 2240624Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[NH:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13](=[O:20])[CH2:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13](=[O:20])[CH2:12][CH2:11][CH2:10]1)=[O:7]

Participants

Conditions

Temperature: 10 °C

Procedure

5-Chlorovaleryl chloride (18.61 mmol, 2.89 g) in dimethylformamide (20 ml) was added dropwise at 10° to a suspension of 1,2,3,4-tetrahydro-5H-1-benzazepin-5-one (12.41 mmol, 2.00 g, preparation according to J. Org. Chem 1972, 37, 2849) and potassium carbonate (14.89 mmol, 2.06 g) in dimethylformamide (40 ml). The reaction mixture was stirred first at 10° C. for 1 h and then under reflux for 3 h. The precipitated salts were filtered off and the filtrate was concentrated to dryness. CH2Cl2 was added to the oil obtained in this way and the mixture was washed three times with 50 ml each time of a 5% aqueous sodium hydrogencarbonate solution, neutralized with 0.1N HCl (20 ml) and then washed three times with a saturated sodium chloride solution. The organic phase was dried over Na2SO4 and concentrated under reduced pressure; yield 3.90 g (80% pure).

Workup

temperatureunder reflux for 3 h
filtrationThe precipitated salts were filtered off
concentrationthe filtrate was concentrated to dryness
additionCH2Cl2 was added to the oil
customobtained in this way
washthe mixture was washed three times with 50 ml each time of a 5% aqueous sodium hydrogencarbonate solution
washwashed three times with a saturated sodium chloride solution
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-1476836968154e4e9cffcfd57b52adf9
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723384B2

Reaction notes

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