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

HRID 227550ノート

反応式

HRID 227550 の反応式
[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

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471Triethylamine2 回HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 154604002-[3-(3,4-Dichlorophenyl)piperidin-3-yl]ethanol

生成物 1

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

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
2.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-90b4d41b485d468dadfdeaf19bfb40e9
出典データセット
uspto-grants-2009_07
特許番号
US07560549B2

反応ノート

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