Nitrogen → (2,6-Dimethoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)phenyl]-methanone

HRID 732800

반응식

HRID 732800 반응식
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[CH:4]=1.N#N.[N:17]1([CH2:23][CH2:24][O:25][C:26]2[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.O>[CH3:14][O:13][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]=1[C:30]([C:29]1[CH:28]=[CH:27][C:26]([O:25][CH2:24][CH2:23][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:34][CH:33]=1)=[O:31]

참가 물질

7

반응물 4

HCID 947NitrogenHCID 796272,6-DimethoxynaphthaleneHCID 6451240Aluminum(III) ChlorideHCID 111190664-(2-(Piperidin-1-yl)ethoxy)benzoyl chloride

생성물 1

HCID 11654660(2,6-Dimethoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)phenyl]-methanone

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

Dissolve 2,6-dimethoxynaphthalene (1.0 eq.) in CH2Cl2 (5 volume eq.) at ambient temperature in a dry round bottom flask equipped with stir bar, temperature probe and N2 line. Cool the solution to 0° C. with an ice bath, and add 4-(2-piperidin-1-yl-ethoxy)-benzoyl chloride (1.1 eq.). Add aluminum chloride (2.0 eq.). Once the reaction is determined to be complete, quench the reaction slowly with 1 N NaOH and dilute with additional water and CH2Cl2. Wash the aqueous layer with CH2Cl2 (20 mL). Combine the organic extracts and wash with brine and dry (Na2SO4). Recrystallize the crude product from methanol to give (2,6-dimethoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone.

후처리

  1. customequipped
  2. customquench
  3. customthe reaction slowly with 1 N NaOH
  4. washWash the aqueous layer with CH2Cl2 (20 mL)
  5. washCombine the organic extracts and wash with brine
  6. dry with materialdry (Na2SO4)
  7. customRecrystallize the crude product from methanol

출처 및 근거

ORD 기록
ord-6a315c8799e24217b88eff3e7bb0dbda
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585977B2

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