Potassium Carbonate → 2-(5-{3-[4-(2-Chloro-phenoxy)-piperidin-1-yl]-propylidene}-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl)-propan-2-ol

HRID 556990노트

반응식

HRID 556990 반응식
Cl.[Cl:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.Br[CH2:17][CH2:18][CH:19]=[C:20]1[C:26]2[CH:27]=[CH:28][CH:29]=[N:30][C:25]=2[CH2:24][O:23][C:22]2[CH:31]=[CH:32][C:33]([C:35]([OH:38])([CH3:37])[CH3:36])=[CH:34][C:21]1=2.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[Cl:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:17][CH2:18][CH:19]=[C:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[N:30][C:25]=3[CH2:24][O:23][C:22]3[CH:31]=[CH:32][C:33]([C:35]([OH:38])([CH3:37])[CH3:36])=[CH:34][C:21]2=3)[CH2:8][CH2:7]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 167325894-(2-Chlorophenoxy)piperidine hydrochlorideHCID 666859992-[5-(3-Bromo-propylidene)-5,1 1-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol

생성물 1

HCID 667576402-(5-{3-[4-(2-Chloro-phenoxy)-piperidin-1-yl]-propylidene}-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl)-propan-2-ol수율 68%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

4-(2-Chloro-phenoxy)-piperidine hydrochloride (0.067 g, 0.268 mmol) was dissolved in a mixture of acetonitrile (1.32 mL) and water (0.17 mL). To this mixture was added 2-[5-(3-Bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (0.050 g, 0.134 mmol) and potassium carbonate (0.074 g, 0.536 mmol). The mixture was stirred at room temperature for 24 hrs and then concentrated in vacuo. The resulting white solid was suspended in ethyl acetate (5 mL) and an equal volume of water was added. The product was extracted into ethyl acetate (2×5 mL). The pooled organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford an oil. The residue was purified by silica gel chromatography (ethyl acetate to 87/10/3 ethyl acetate/methanol/triethylamine gradient) to afford the title compound (46 mg, 68%).

후처리

  1. concentrationconcentrated in vacuo
  2. additionan equal volume of water was added
  3. extractionThe product was extracted into ethyl acetate (2×5 mL)
  4. dry with materialThe pooled organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford an oil
  8. customThe residue was purified by silica gel chromatography (ethyl acetate to 87/10/3 ethyl acetate/methanol/triethylamine gradient)

출처 및 근거

ORD 기록
ord-02951b0ae33642f98dc5e71e6269f41b
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058287B2

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