Indolin-1-amine hydrochloride → HCID 20066538, compound

HRID 358566Notes

Reaction equation

HRID 358566 reaction equation
Cl.N[N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.[O:12]=[C:13]1[CH2:18][C:17](=O)[CH2:16][CH2:15][NH:14]1>C(O)C>[CH:9]1[CH:8]=[CH:7][C:6]2[CH2:5][CH2:4][N:3]3[C:11]=2[C:10]=1[C:18]1[C:13](=[O:12])[NH:14][CH2:15][CH2:16][C:17]=13

Participants

4

Reactant 2

HCID 2760931Indolin-1-amine hydrochlorideHCID 108878632,4-Piperidinedione

Product 1

HCID 20066538HCID 20066538, compoundYield 201%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-amino-indoline hydrochloride (1.0 g) and 2,4-dioxopiperidine (663 mg) in absolute ethanol (40 ml) was stirred under nitrogen for 48 h. The solvent was removed in vacuo and the residue was dissolved in diethylene glycol (30 ml) and heated at 200° for 2 h. The solution was allowed to cool, poured into water (200 ml) and extracted with dichloromethane (3×100 ml). The combined, dried organic extracts were evaporated to give an oil (ca. 2.5 g) which was purified by short path column chromatography on silica gel (Merck 7729) eluting with System A (400:10:1) to give the title compound (330 mg) as a solid, m.p. 265°-267°.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in diethylene glycol (30 ml)
  3. temperatureheated at 200° for 2 h
  4. temperatureto cool
  5. additionpoured into water (200 ml)
  6. extractionextracted with dichloromethane (3×100 ml)
  7. customdried organic extracts were evaporated

Sources & evidence

ORD record
ord-2940da54f1474d00b50aaa2687c119c8
Source dataset
uspto-grants-1991_03
Patent number
US04997831

Reaction notes

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