Hydrochloric Acid → 1-(2-Formamidophenyl)-1'-methylspiro[indoline-3,4'-piperidine] hydrochloride

HRID 1660361

반응식

HRID 1660361 반응식
[ClH:1].Cl.[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]2([CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[CH2:11]1.[CH3:25][O-:26].[Na+].Cl>CN(C)C=O.CCOCC>[ClH:1].[CH:25]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]2([CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[CH2:11]1)=[O:26]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 128015981-(2-Aminophenyl)-1'-methylspiro[indoline-3,4'-piperidine]dihydrochloride

생성물 1

HCID 128016041-(2-Formamidophenyl)-1'-methylspiro[indoline-3,4'-piperidine] hydrochloride

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a mixture of 15.0 g of 1-(2-aminophenyl)-1'-methylspiro[indoline-3,4'-piperidine]dihydrochloride, Example 16, in 75 ml of dimethylformamide at 90° C. under nitrogen is added 8.6 g of sodium methoxide. Following this addition the reaction temperature is increased to 110°-115° C. and maintained at this temperature for 40 minutes. The resulting dark brown mixture is permitted to cool to 90° C. and then poured onto 800 ml of icewater. The mixture is filtered and the filter cake is washed with water and then dissolved in chloroform. The chloroform solution is successively washed with brine, dried and concentrated leaving a red colored glass. The glass is dissolved in ether, where it is converted to its hydrochloric acid salt which is collected by filtration and then washed with ether and finally dried. The salt is recrystallized from a methyl alchol-ether mixture to provide the product, mp 287.5° C., dec of 1-(2-formamidophenyl)-1'-methylspiro[indoline-3,4'-piperidine]hydrochloride.

후처리

  1. additionthis addition the reaction temperature
  2. temperatureis increased to 110°-115° C.
  3. temperaturemaintained at this temperature for 40 minutes
  4. additionpoured onto 800 ml of icewater
  5. filtrationThe mixture is filtered
  6. washthe filter cake is washed with water
  7. dissolutiondissolved in chloroform
  8. washThe chloroform solution is successively washed with brine
  9. customdried
  10. concentrationconcentrated
  11. customleaving a red colored glass
  12. filtrationis collected by filtration
  13. washwashed with ether
  14. customfinally dried
  15. customThe salt is recrystallized from a methyl alchol-ether mixture

출처 및 근거

ORD 기록
ord-c0c86c98644a4535904ee7bee3af7172
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04307235

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