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

HRID 1660366노트

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HRID 1660366 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 80711,2-Dimethoxyethane용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-512000dc17b0478d875ec9d3ec5f27a8
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04307235

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