Hydrochloric Acid → Benzonitrile, 2-(2-hydroxy-3-((2-(1H-indol-3-yl)-1,1-dimethylethyl)amino)propoxy)-, hydrochloride (1:1)

HRID 224887

反応式

HRID 224887 の反応式
O1CC1COC1C=CC=CC=1C#N.N1C2C(=CC=CC=2)C(CC(N)(C)C)=C1.[CH3:28][C:29]([N:41](CC(O)COC1C=CC=CC=1C#N)[CH2:42][CH:43]([OH:54])[CH2:44][O:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52]#[N:53])([CH3:40])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1.[ClH:68]>CC(O)C.CO.CCO>[ClH:68].[OH:54][CH:43]([CH2:42][NH:41][C:29]([CH3:40])([CH3:28])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)[CH2:44][O:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52]#[N:53]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 93531-(1H-indol-3-yl)-2-methylpropan-2-amineHCID 126196712-(Oxiran-2-ylmethoxy)benzonitrileHCID 233305231,1'-[[1,1-dimethyl-2-(1H-indol-3yl)ethyl]imino]bis[3-(2-cyanophenoxy)-2-propanol]

生成物 1

HCID 51044Benzonitrile, 2-(2-hydroxy-3-((2-(1H-indol-3-yl)-1,1-dimethylethyl)amino)propoxy)-, hydrochloride (1:1)

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 887Methanol溶媒2 回HCID 3776Isopropanol溶媒

実験手順

A solution of 2-[(2,3-epoxy)propoxy]benzonitrile (18.3 g., 0.10 mole) and 2-(3-indolyl)-1,1-dimethylethylamine (15.2 g., 0.08 mole), in 500 ml. of abs. EtOH was stirred at reflux overnight. After concentration of the reaction mixture to approximately 200 ml. and seeding, crude product began to precipitate. The mixture was then cooled and the precipitate separated by filtration to give 24.8 g. of the free base form of the product, white solid, m.p. 120°-123°. The crude solid was dissolved in 400 ml. of boiling MeOH, and the solution was cooled with stirring, as a by-product 1,1'-[[1,1-dimethyl-2-(1H-indol-3yl)ethyl]imino]bis[3-(2-cyanophenoxy)-2-propanol] precipitated. The by-product was collected on a filter and air dried to give 2.2 g., m.p. 180°-187°. The MeOH filtrate was then taken to dryness. The residual solid was dissolved in 200 ml. of i-PrOH and acidified with ethanolic HCl. Seeding followed by 18 hours standing in the cold afforded the product as the crystalline hydrochloride. Filtration of the mixture gave 19.8 g., of solid, m.p. 179°-183°. One recrystallization from abs. EtOH gave 15.5 g. (48%) of white solid, m.p. 185°-187°. TLC on silica gel (9CH2Cl2, 10 MeOH, 1NH4OH) showed a single spot (Rf =0.5, u.v.).

後処理

  1. temperatureat reflux overnight
  2. customto precipitate
  3. temperatureThe mixture was then cooled
  4. customthe precipitate separated by filtration
  5. customto give 24.8 g
  6. dissolutionThe crude solid was dissolved in 400 ml
  7. customprecipitated
  8. customThe by-product was collected on
  9. filtrationa filter
  10. customair dried
  11. customto give 2.2 g
  12. dissolutionThe residual solid was dissolved in 200 ml

出典と根拠

ORDレコード
ord-60072d62dca446e7856bcfc06594aca0
出典データセット
uspto-grants-1980_11
特許番号
US04234595

関連ノート

読み込み中…