Bis(1,3-dichloroisopropyl ether) → 4-[1-(4-Methylphenylsulfonyl)piperidin-4-yl]benzaldehyde

HRID 566084

반응식

HRID 566084 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC[CH:25]([O:28]C(CCl)CCl)CCl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:25]=[O:28])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 93323Bis(1,3-dichloroisopropyl ether)HCID 41684661-[(4-Methylphenyl)sulfonyl]-4-phenylpiperidine

생성물 1

HCID 184726214-[1-(4-Methylphenylsulfonyl)piperidin-4-yl]benzaldehyde

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 1-(4-methylphenylsulfonyl)-4-phenylpiperidine (1.0 g) and 1,1-dichloromethylmethylether (0.57 ml) in dichloromethane (5 ml) was added at 0° C. a solution of titanium tetrachloride (0.7 ml) in dichloromethane (5 ml), and the mixture was stirred at room temperature for 2 hours. The mixture was added to stirred ice/water to stop the reaction. The mixture was extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate solution and saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was purified with column chromatography (ethyl acetate/hexane=1:4→1:2) to give pale yellow crystals of 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]benzaldehyde (0.381 g). (469.4 mg of the starting materials were collected)

후처리

  1. additionThe mixture was added
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with sodium bicarbonate solution and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationUnder reduced pressure, the mixture was concentrated
  7. customthe residue was purified with column chromatography (ethyl acetate/hexane=1:4→1:2)

출처 및 근거

ORD 기록
ord-35a49dfd4eef4eb59e0909da870a2bee
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172061B2

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