Potassium Carbonate → Ethyl 1-benzyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate

HRID 2305874

반응식

HRID 2305874 반응식
Cl.Cl[CH2:3][CH2:4][N:5]([CH2:13][CH2:14]Cl)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1OCCOCCOCCOCCOCCOC1.C([O-])([O-])=O.[K+].[K+].[CH2:40]([O:42][C:43](=[O:56])[CH2:44][S:45]([C:48]1[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=1)(=[O:47])=[O:46])[CH3:41]>CC(C)=O>[CH2:40]([O:42][C:43]([C:44]1([S:45]([C:48]2[CH:49]=[CH:50][C:51]([O:54][CH3:55])=[CH:52][CH:53]=2)(=[O:47])=[O:46])[CH2:14][CH2:13][N:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:4][CH2:3]1)=[O:56])[CH3:41]

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 14823722-[(4-Methoxyphenyl)sulfonyl]acetic acid ethyl esterHCID 2777881N,N-Bis(2-chloroethyl)benzylamine hydrochloride

생성물 1

HCID 3695010Ethyl 1-benzyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a stirred solution of bis-(2-chloro-ethyl)-benzyl amine hydrochloride (6.6 g, 24.7 mmol), 18-Crown-6 (500 mg), and anhydrous K2CO3 (30 gmn, excess) in dry acetone (250 ml), (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester (6.12 gm, 24 mmol) was added in a round bottom flask and the reaction mixture was heated at reflux for 16 hours with good stirig. At the end, the reaction miixture was allowed to cool and the potassium salts were filtered off and the reaction mixture was concentrated. The residue was extracted with chloroform and washed with H2O. The organic layer was furher washed well with water, dried over MgSO4, fitered and concentrated. The dark brown reaction mixture was purified by silica gel couinn chromatography by eluting it with 30% ethylace tate: hexane and the product 4-(4-Methoxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid ethyl ester was isolated as Brown oil. Yield: 6.0 g, 60%; MS: 418 (M+H).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 hours with good stirig
  3. temperatureto cool
  4. filtrationthe potassium salts were filtered off
  5. concentrationthe reaction mixture was concentrated
  6. extractionThe residue was extracted with chloroform
  7. washwashed with H2O
  8. washThe organic layer was furher washed well with water
  9. dry with materialdried over MgSO4
  10. concentrationfitered and concentrated
  11. customThe dark brown reaction mixture was purified by silica gel couinn chromatography
  12. washby eluting it with 30% ethylace tate

출처 및 근거

ORD 기록
ord-581ebd412bbb480e9bf355386d9c539a
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06441023B1

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