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 457122ノート

反応式

HRID 457122 の反応式
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

参加物

6

反応物 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

生成物 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-ol収率 68%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-8f51c193f518442b9631f5da505ee71e
出典データセット
uspto-grants-2007_03
特許番号
US07186729B2

反応ノート

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