Hydrochloric Acid → 4-(4-Chloro-3-fluorobenzyl)morpholine

HRID 1924016

반응식

HRID 1924016 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[F:10].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClC(Cl)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:4][C:3]=1[F:10]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 27249854-Chloro-3-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 595438604-(4-Chloro-3-fluorobenzyl)morpholine수율 60.4%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

4-Chloro-3-fluorobenzaldehyde (1.0 g, 6.31 mmol), morpholine (0.546 ml, 6.31 mmol) and sodium triacetoxyborohydride (1.938 g, 9.14 mmol) were mixed in dichloroethane (19 ml) and the reaction stirred at ambient temperature under an atmosphere of argon over night. 1M HCl (aq, 25 ml) was added. The mixture was extracted with dichloromethane (×4). The pH was adjusted to ca 12 by adding KOH (s). The mixture was extracted with dichloromethane (×4). The combined organic phases were dried over MgSO4 filtered and concentrated in vacuo to give 4-(4-chloro-3-fluorobenzyl)morpholine (0.875 g, 60%) as a liquid.

후처리

  1. extractionThe mixture was extracted with dichloromethane (×4)
  2. additionby adding KOH (s)
  3. extractionThe mixture was extracted with dichloromethane (×4)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5bff997b060e46a2b820e73238a8ebc3
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178529B2

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