1-Chloroethyl chloroformate → 2-[4-(2,6-Dichloro-phenoxymethyl)-phenyl]-morpholine

HRID 2167874노트

반응식

HRID 2167874 반응식
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])=[CH:16][CH:15]=2)[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[Cl:28][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:29])[C:22]=1[O:21][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([CH:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:19][CH:18]=1

참가 물질

4

반응물 2

HCID 5213051-Chloroethyl chloroformateHCID 670325914-Benzyl-2-[4-(2,6-dichloro-phenoxymethyl)-phenyl]-morpholine

생성물 1

HCID 670324202-[4-(2,6-Dichloro-phenoxymethyl)-phenyl]-morpholine수율 78.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 4-benzyl-2-[4-(2,6-dichloro-phenoxymethyl)-phenyl]-morpholine (2.25 g; 3.7 mmol) in 1,2-dichloroethane (10 mL), was added dropwise 1-chloroethyl chloroformate (0.44 mL; 4.0 mmol), at 0° C. After 15 minutes, the cooling was removed and subsequently the mixture was heated under reflux overnight. After cooling to RT the mixture was concentrated in vacuo. To the residue was added toluene and the mixture was concentrated in vacuo. This last step was repeated twice. To the final residue was added MeOH (10 mL), and this mixture was stirred overnight at RT. Once more the mixture was concentrated in vacuo. The residue was partitioned between EtOAc and 2 M Aqueous NaOH. The layers were separated, and the organic layer dried (Na2SO4), filtered, and concentrated in vacuo to afford 2-[4-(2,6-Dichloro-phenoxymethyl)-phenyl]-morpholine (0.98 g), which was used as such in the next step.

후처리

  1. customat 0° C
  2. customthe cooling was removed
  3. temperaturesubsequently the mixture was heated
  4. temperatureunder reflux overnight
  5. concentrationwas concentrated in vacuo
  6. additionTo the residue was added toluene
  7. concentrationthe mixture was concentrated in vacuo
  8. additionTo the final residue was added MeOH (10 mL)
  9. concentrationOnce more the mixture was concentrated in vacuo
  10. customThe residue was partitioned between EtOAc and 2 M Aqueous NaOH
  11. customThe layers were separated
  12. dry with materialthe organic layer dried (Na2SO4)
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0101a98ecd53429e931a094c967f873a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045441B2

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