Hydrochloric Acid → 2-[3-(3,4-Dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)piperidin-3-yl]ethyl 4-chlorobenzenesulfonate

HRID 227550노트

반응식

HRID 227550 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:15][CH2:16][OH:17])[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([O:38][CH3:39])[C:35]=1[O:36][CH3:37])[C:30](Cl)=[O:31].[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1.Cl>O1CCCC1.CN(C)C1C=CN=CC=1.C(Cl)Cl.O>[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([S:47]([O:17][CH2:16][CH2:15][C:9]2([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH2:14][CH2:13][CH2:12][N:11]([C:30](=[O:31])[C:29]3[CH:28]=[C:27]([O:26][CH3:25])[C:35]([O:36][CH3:37])=[C:34]([O:38][CH3:39])[CH:33]=3)[CH2:10]2)(=[O:49])=[O:48])=[CH:43][CH:42]=1

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471Triethylamine2회HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 154604002-[3-(3,4-Dichlorophenyl)piperidin-3-yl]ethanol

생성물 1

HCID 111580092-[3-(3,4-Dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)piperidin-3-yl]ethyl 4-chlorobenzenesulfonate수율 76.3%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
2.5 °C

실험 절차

To a solution of (+)-2-[3-(3,4-dichlorophenyl)piperidin-3-yl]ethanol (1.70 g, 6.20 mmol) in tetrahydrofuran (85 ml) was added triethylamine (1.30 ml, 9.35 mmol), and the resulting mixture was cooled to 0-5° C. After cooling, a solution of 3,4,5-trimethoxybenzoyl chloride (1.46 g, 6.33 mmol) in tetrahydrofuran (7 ml) was further added dropwise at below 5° C., and the resulting mixture was stirred at 0-5° C. for 5 hours and then evaporated to dryness in vacuo. Subsequently, to the residue obtained were added methylene chloride (50 ml), triethylamine (1.30 ml, 9.35 mmol) and 4-dimethylaminopyridine (0.076 g, 0.62 mmol), and the resulting mixture was cooled to 0-5° C. After cooling, a solution of 4-chlorobenzenesulfonyl chloride (1.57 g, 7.44 mmol) in methylene chloride (3.5 ml) was further added dropwise at below 5° C., and the resulting mixture was stirred at 0-5° C. for 5 hours. After completion of the reaction, water (50 ml) and concentrated hydrochloric acid (2 ml) were added to the reaction mixture, and the resulting mixture was partitioned. The separated organic layer was washed with water (50 ml) and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column and then crystallized from a mixed solvent of ethyl acetate (6.6 ml) and hexane (17.7 ml) under ice-cooling to afford the title compound [3.0 g, yield: 76.3%] as a colorless crystalline solid.

후처리

  1. temperatureAfter cooling
  2. customevaporated to dryness in vacuo
  3. customSubsequently, to the residue obtained
  4. temperaturethe resulting mixture was cooled to 0-5° C
  5. temperatureAfter cooling
  6. stirringthe resulting mixture was stirred at 0-5° C. for 5 hours
  7. additionwere added to the reaction mixture
  8. customthe resulting mixture was partitioned
  9. washThe separated organic layer was washed with water (50 ml)
  10. customevaporated in vacuo
  11. customThe residue obtained
  12. customwas purified by chromatography on a silica gel column
  13. customcrystallized from a mixed solvent of ethyl acetate (6.6 ml) and hexane (17.7 ml) under ice-
  14. temperaturecooling

출처 및 근거

ORD 기록
ord-90b4d41b485d468dadfdeaf19bfb40e9
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560549B2

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