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

HRID 1632867노트

반응식

HRID 1632867 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

반응 조건

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 100 ml 6M 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 contrated 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-770c4bf44c4345afa216838f3802fa3b
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04477667

반응 노트

불러오는 중…