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Diethyl Ether → 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-urea

HRID 1394266
ノート
印刷プレビュー

反応式

HRID 1394266 の反応式
[CH3:1][N:2]([CH3:32])[C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([NH:13][CH:14]([CH3:25])[CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:12])[CH2:5][CH2:4]1.[Cl:33][Si](C)(C)C.C(OCC)C>CC(CC)=O>[ClH:33].[CH3:32][N:2]([CH3:1])[C:3]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([NH:13][CH:14]([CH3:25])[CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:12])[CH2:5][CH2:4]1.[CH3:32][N:2]([CH3:1])[C:3]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([NH:13][CH:14]([CH3:25])[CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:12])[CH2:5][CH2:4]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 117544171-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-urea

生成物 2

HCID 117544161-(4-Dimethylamino-4-phenylcyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]urea hydrochlorideHCID 117544171-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-urea
収率 209.3%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl-methyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-urea (157 mg, 0.36 mmole) was dissolved in ethyl methyl ketone (6 ml). Chlorotrimethylsilane (69 μl, 0.6 mmole) was added dropwise with stirring at RT. On stirring for one hour at RT, only a little precipitate formed. The reaction solution was combined with diethyl ether (25 ml). The mixture was then vigorously stirred at RT for 1 h. A colorless precipitate was formed. The solid was filtered out, washed with diethyl ether (3×2 ml) and dried under a vacuum. The hydrochloride of the more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-urea (163 mg, m.p. 150-155° C., 97%; Example 25) was obtained in this manner as a colorless solid.

後処理

  1. stirringOn stirring for one hour at RT
  2. customonly a little precipitate formed
  3. stirringThe mixture was then vigorously stirred at RT for 1 h
  4. customA colorless precipitate was formed
  5. filtrationThe solid was filtered out
  6. washwashed with diethyl ether (3×2 ml)
  7. customdried under a vacuum

出典と根拠

ORDレコード
ord-d0235be16e8e4e71b29e50596fd8a992
出典データセット
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07348354B2

反応ノート

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