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

HRID 1350510ノート

反応式

HRID 1350510 の反応式
Cl.[CH3:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]([NH2:13])=[N:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7]=2[CH:18]=1.[CH2:19]([C@H:27]1[CH2:32]N[CH2:30][CH2:29][NH:28]1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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:13]3[CH2:30][CH2:29][NH:28][C@@H:27]([CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:32]3)=[N:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7]=2[CH:18]=1

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 210935233-Methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochlorideHCID 44828673(S)-2-Phenethylpiperazine

生成物 1

HCID 588606203-Methyl-11-[(S)-3-phenethyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine収率 85%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

Combine 3-methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride (400.0 mg, 1.54 mmol), (S)-2-phenethyl-piperazine (879.1 mg, 4.62 mmol), N,N-diisopropylethylamine (199.0 mg, 1.54 mmol), DMSO (0.7 ml), and toluene (2.8 ml). Stir and heat the mixture at 110° C. After 65 hours, cool the mixture to ambient temperature and then dilute it with ethyl acetate. Wash the organic layer with 0.1 N 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 518.7 mg (85%) of a tan foam: mp 64°–80°; mass spectrum (ion spray): m/z=397.2 (M+1).

後処理

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

出典と根拠

ORDレコード
ord-0a104ec81a4f481a9c2749d7a33cc640
出典データセット
uspto-grants-2007_05
特許番号
US07214673B2

反応ノート

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