Benzyl Chloride → 1-benzylindoline

HRID 1413942Notes

Reaction equation

HRID 1413942 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[CH2:16]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 10328IndolineHCID 11430Potassium Carbonate

Product 1

HCID 108050961-benzylindolineYield 73.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred refluxing mixture of 119 g (1 mole) of indoline, 800 ml of toluene (other solvents, e.g. isopropyl alcohol, are satisfactory), and 207 g (1.5 mole) of pulverized, anhydrous potassium carbonate is added dropwise 126.5 g (1 mole) of benzyl chloride. When addition is complete, refluxing is continued until evolution of gas ceases as evidenced by a gas meter (about three hours). The mixture is allowed to cool, and the solids are removed by filtration. The filtrate is evaporated, and the residue is distilled to give 153 g (73%) of 1-benzylindoline, b.p. 162°-165° (4.5 mm).

Workup

  1. temperatureTo a stirred refluxing
  2. additionWhen addition
  3. temperaturerefluxing
  4. customas evidenced by a gas meter (about three hours)
  5. temperatureto cool
  6. customthe solids are removed by filtration
  7. customThe filtrate is evaporated
  8. distillationthe residue is distilled

Sources & evidence

ORD record
ord-b02fc3c04be446e99f21e22790226c64
Source dataset
uspto-grants-1981_02
Patent number
US04251659

Reaction notes

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