Water → 1-benzylindoline

HRID 1108478Notes

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.[Na+].O.[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

Conditions

Temperature: 90 °C

Procedure

Into a 1,000 mλ reaction flask equipped with a thermometer, a stirrer, a condenser and a dropping funnel, 119.2 g (1.0 mol) of indoline, 105 g (1.25 mols) of sodium hydrogen carbonate and 200 g of water were charged, and the temperature was raised to a liquid temperature of 90° C. Then, while stirring at the same temperature, 132.9 g (1.05 mols) of benzyl chloride was dropwise added thereto over a period of about one hour from the dropping funnel, and then stirring was continued for eight hours at from 90 to 95° C. After completion of the reaction, 400 mλ of toluene was added, and the mixture was stirred from 60 to 80° C. for a while and then left to stand still for liquid separation. From the obtained organic layer, toluene was distilled off under reduced pressure to obtain 209 g of brown 1-benzylindoline (crude yield: 100%).

Workup

customInto a 1,000 mλ reaction flask
additionwere charged
additionwas dropwise added
waitwas continued for eight hours at from 90 to 95° C
additionwas added
stirringthe mixture was stirred from 60 to 80° C. for a while
waitleft
customto stand still for liquid separation
distillationFrom the obtained organic layer, toluene was distilled off under reduced pressure

Sources & evidence

ORD record: ord-d56bb26275dc44de980d5de2e8fffaaf
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06066744

Reaction notes

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