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

HRID 1707124

Reaction equation

HRID 1707124 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-af4761d265384c9d8148ff2b58cb422c
Source dataset
uspto-grants-1980_06
Patent number
US04209625

Linked notes

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