Chloroacetyl chloride → 4-Benzyl-6-(4-bromo-phenyl)-morpholin-3-one

HRID 571769ノート

反応式

HRID 571769 の反応式
[CH2:1]([NH:8][CH2:9][CH:10]([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.Cl[CH2:27][C:28](Cl)=[O:29].[OH-].[K+]>C(Cl)Cl>[CH2:1]([N:8]1[CH2:9][CH:10]([C:12]2[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=2)[O:11][CH2:27][C:28]1=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 580978892-Benzylamino-1-(4-bromo-phenyl)-ethanol

生成物 1

HCID 580978854-Benzyl-6-(4-bromo-phenyl)-morpholin-3-one収率 103.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-benzylamino-1-(4-bromo-phenyl)-ethanol (18.95 g; 62 mmol) and Et3N (9.6 mL; 68 mmol) in CH2Cl2 (500 mL) was added dropwise a solution of chloroacetyl chloride (5.4 mL; 68 mmol) in CH2Cl2 (20 mL), at 0° C. After 1 hour at 0° C. the reaction mixture was quenched with 1M aqueous HCl (200 mL). The layers were separated and the organic layer washed with a 5% aqueous NaHCO3 solution, dried (Na2SO4) and concentrated in vacuo. The residue was dissolved in 2-propanol (200 mL) and KOH (4.2 g; 75 mmol) was added. The resulting mixture was stirred at RT for 3 hours and subsequently concentrated in vacuo. The crude product was partitioned between CH2Cl2 and 1M aqueous HCl. The layers were separated and the organic layer was washed with saturated aqueous NaHCO3 solution, dried (Na2SO4) and evaporated in vacuo to afford 4-benzyl-6-(4-bromo-phenyl)-morpholin-3-one (22.30 g) which was used as such in the next step.

後処理

  1. customat 0° C
  2. customAfter 1 hour at 0° C. the reaction mixture was quenched with 1M aqueous HCl (200 mL)
  3. customThe layers were separated
  4. washthe organic layer washed with a 5% aqueous NaHCO3 solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in 2-propanol (200 mL)
  8. concentrationsubsequently concentrated in vacuo
  9. customThe crude product was partitioned between CH2Cl2 and 1M aqueous HCl
  10. customThe layers were separated
  11. washthe organic layer was washed with saturated aqueous NaHCO3 solution
  12. dry with materialdried (Na2SO4)
  13. customevaporated in vacuo

出典と根拠

ORDレコード
ord-6c817a92e27a4d2c9b14b41ef9fbcc6a
出典データセット
uspto-grants-2015_05
特許番号
US09029371B2

反応ノート

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