Dimethyl Sulfoxide → 2-Methyl-11-(4-methyl-piperazin-1-yl)-3-methyl-5H-dibenzo[b,e][1,4]diazepine

HRID 1350514노트

반응식

HRID 1350514 반응식
Cl.[CH3:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[N:10]=[C:11]([NH2:12])[C:5]=2[CH:4]=1.[CH3:19][N:20]1[CH2:25][CH2:24]N[CH2:22][CH2:21]1.[CH:26](N(CC)C(C)C)(C)C.CS(C)=O>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:2][C:3]1[C:18]([CH3:26])=[CH:17][C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[N:10]=[C:11]([N:12]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)[C:5]=2[CH:4]=1

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 210935072-Methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride

생성물 1

HCID 210934982-Methyl-11-(4-methyl-piperazin-1-yl)-3-methyl-5H-dibenzo[b,e][1,4]diazepine수율 78%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

Combine 2-methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride (600.0 mg, 2.31 mmol), N-methylpiperazine (1.39 g, 13.86 mmol), N,N-diisopropylethylamine (298.6 mg, 2.31 mmol), DMSO (1.0 ml), and toluene (4.0 ml). Stir and heat the mixture at 110° C. After 48 hours, cool the mixture to ambient temperature and stir it overnight. Dilute the mixture with ethyl acetate and wash the organic layer with 0.1N NaOH and brine. Dry (sodium sulfate) and concentrate the organic layer to residue. Purify the residue on silica gel using dichloromethane/methanol (90:10) to give 550.5 mg (78%) of a tan foam: mp 170°–177°, dec; mass spectrum (ion spray): m/z=307.2 (M+1).

후처리

  1. temperaturecool the mixture to ambient temperature
  2. stirringstir it overnight
  3. washwash the organic layer with 0.1N NaOH and brine
  4. dry with materialDry (sodium sulfate)
  5. concentrationconcentrate the organic layer to residue
  6. customPurify the residue on silica gel

출처 및 근거

ORD 기록
ord-88e54ce9c03740f3a94b95b547bf4700
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07214673B2

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