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

HRID 1924016

反応式

HRID 1924016 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 595438604-(4-Chloro-3-fluorobenzyl)morpholine収率 60.4%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5bff997b060e46a2b820e73238a8ebc3
出典データセット
uspto-grants-2012_05
特許番号
US08178529B2

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