N-(1-benzoyl-4-piperidinyl)-2-(2-carbamoylethyl)aniline → 1-(1-Benzoyl-piperidin-4-yl)-3,4-dihydro-1H-quinolin-2-one

HRID 1648551Notes

Reaction equation

HRID 1648551 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][CH2:23][C:24](=[O:26])N)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl>[C:1]([N:9]1[CH2:10][CH2:11][CH:12]([N:15]2[C:16]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:22][CH2:23][C:24]2=[O:26])[CH2:13][CH2:14]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 19031102N-(1-benzoyl-4-piperidinyl)-2-(2-carbamoylethyl)aniline

Product 1

HCID 149695101-(1-Benzoyl-piperidin-4-yl)-3,4-dihydro-1H-quinolin-2-oneYield 43.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To N-(1-benzoyl-4-piperidinyl)-2-(2-carbamoylethyl)aniline (85 g) prepared in Reference Example 4 is added 5 % hydrochloric acid (500 ml) and the mixture is refluxed for 5 hours. After cooling, the reaction mixture is extracted with diethyl ether and the aqueous layer is made alkaline with a 50 % aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract is dried over sodium carbonate and concentrated. The concentrate is purified by silica gel column chromatography (eluent; n-hexane/ethyl acetate=1/0-10/1) and recrystallized from ethanol/n-hexane to give 1-(1-benzoyl-4-piperidinyl)-3,4-dihydrocarbostyril (35 g) as white powders, m.p. 108°-111° C.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture is extracted with diethyl ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract is dried over sodium carbonate
  6. concentrationconcentrated
  7. customThe concentrate is purified by silica gel column chromatography (eluent; n-hexane/ethyl acetate=1/0-10/1)
  8. customrecrystallized from ethanol/n-hexane

Sources & evidence

ORD record
ord-8eae244960cd462a911ac4558653566f
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

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