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

HRID 131416
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인쇄 미리보기

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HRID 131416 반응식
Cl.[CH3:2][C:3]1[CH:4]=[C:5](N)[C:6]2[CH:12]=[N:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[NH:8][C:7]=2[CH:17]=1.[CH3:19][O:20][CH2:21][CH2:22][C@H:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1.C(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[CH:4]=[CH:5][C:6]2[C:12]([N:27]3[CH2:26][CH2:25][NH:24][C@@H:23]([CH2:22][CH2:21][O:20][CH3:19])[CH2:28]3)=[N:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[NH:8][C:7]=2[CH:17]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 210935253-methyl-5H-dibenzo[b,e][1,4]diazepin-1-ylamine hydrochlorideHCID 55287560(S)-2-(2-Methoxyethyl)piperazine

생성물 1

HCID 58626009(S)-3-Methyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine수율 48%

시약·촉매·용매 2

HCID 1140
Toluene
용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

Combine 3-methyl-5H-dibenzo[b,e][1,4]diazepin-1-ylamine hydrochloride (400.0 mg, 1.54 mmol), (S)-2-(2-methoxy-ethyl)-piperazine (444.2 mg, 3.08 mmol), N,N-diisopropylethylamine (199.0 mg, 1.54 mmol), DMSO (0.7 ml), and toluene (2.8 ml) and stir and heat the mixture at 110° C. After 48 hours, cool the mixture to ambient temperature and dilute with ethyl acetate. 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 257.1 mg (48%) of a yellow foam: mp=64° C. dec; mass spectrum (ion spray): m/z =433.1 (M+1).

후처리

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

출처 및 근거

ORD 기록
ord-799c2269df80402989ecd0378d73e031
출처 데이터셋
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07384934B2

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