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

HRID 1632862

反応式

HRID 1632862 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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 ice-water. 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 alcohol-ether mixture to provide the product, mp 287.5° C., dec of 1-(2-formamidophenyl)-1'-methylspiro[indoline-3,4'-piperidine] hydrochloride.

後処理

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

出典と根拠

ORDレコード
ord-9fcb1c40465a43649cd770f9faf75304
出典データセット
uspto-grants-1984_10
特許番号
US04477667

関連ノート

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