Sodium Hydroxide → 1'-Carbamoyl-1-(2-nitrophenyl)spiro[indoline3,4'-piperidine]

HRID 1660366ノート

反応式

HRID 1660366 の反応式
[C:1]([N:3]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-:25])=[O:24])[CH2:9]2)[CH2:5][CH2:4]1)#[N:2].[OH-:26].[Na+]>C(COC)OC.Cl>[C:1]([N:3]1[CH2:4][CH2:5][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-:25])=[O:24])[CH2:9]2)[CH2:7][CH2:8]1)(=[O:26])[NH2:2]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 128016151'-Cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]

生成物 1

HCID 128016451'-Carbamoyl-1-(2-nitrophenyl)spiro[indoline3,4'-piperidine]

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
0 °C

実験手順

9.93 g of 1'-cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine] of Example 37 in 150 ml glyme and 100ml 6 M aqueous hydrochloric acid is heated at reflux under nitrogen for 1.5 hours. The mixture is cooled to 0° C., made basic with 50% aqueous sodium hydroxide (40 ml) and concentrated. The residue is dissolved in hot chloroform, washed with saturated sodium chloride, dried over anhydrous magnesium sulfate and contacted to give a crude product. Recrystallization from hot dimethylsulfoxide-dioxane-ether affords 1'-carbamoyl-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine], mp 217.5°-219.0° C.

後処理

  1. temperatureat reflux under nitrogen for 1.5 hours
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in hot chloroform
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customto give a crude product
  7. customRecrystallization from hot dimethylsulfoxide-dioxane-ether

出典と根拠

ORDレコード
ord-512000dc17b0478d875ec9d3ec5f27a8
出典データセット
uspto-grants-1981_12
特許番号
US04307235

反応ノート

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