Sodium Carbonate → 4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

HRID 1773858노트

반응식

HRID 1773858 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[CH2:9]([N:17]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:19]=[C:18]1[CH:28]=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>CS(O)(=O)=O.C(Cl)(Cl)Cl>[CH3:8][N:5]1[CH2:6][CH2:7][CH:2]([O:1][CH:28]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:10][CH2:9][N:17]3[C:18]2=[N:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:21]3)[CH2:3][CH2:4]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 660484-Piperidinol, 1-methyl-HCID 867039471-Phenethyl-4-phenyl-imidazole-2-carbaldehyde

생성물 1

HCID 726957794-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6395Methanesulfonic Acid용매

실험 절차

To a solution of 4-hydroxy-N-methylpiperidine (275 mg, 2.39 mmoles) in methanesulfonic acid (2 mL) at 0° C. is added a solution of 1-phenethyl-4-phenyl-imidazole-2-carbaldehyde (example 4B) (250 mg, 0.904 mmoles) in chloroform (2 mL). The reaction mixture is stirred at room temperature overnight, then heated to reflux for 6 h. A saturated solution of Na2CO3 is added to reach pH 10. The aqueous phase is extracted three times with CH2Cl2. The organic phase is dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (CH2Cl2:MeOH) (90:10) to give 4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene melting at 113° C.

후처리

  1. temperatureheated
  2. temperatureto reflux for 6 h
  3. extractionThe aqueous phase is extracted three times with CH2Cl2
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-a98f6ab652fb447c90e4a58ed8cc0356
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255101B2

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