Hydrochloric Acid → Spiro[indoline-3,3'-perhydroazepin]-2-one

HRID 1835853Notes

Reaction equation

HRID 1835853 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][C:14]1=[O:22])C1C=CC=CC=1.Cl>CS(C)=O.CO>[NH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]2=[O:22])[CH2:1]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 235007413-(4-(Benzylamino)-butyl)-indolin-2-one

Product 1

HCID 23500655Spiro[indoline-3,3'-perhydroazepin]-2-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-(4-(Benzylamino)-butyl)-indolin-2-one. Conc hydrochloric acid (90 mL) was added to a solution of the compound from the previous step in DMSO (38 mL) and MeOH (8 mL). After stirring for 30 min at 0° C. and 30 min at room temperature the mixture was poured onto ice followed by extractive work-up. The title compound was obtained as a crude orange oil (16.2 g).

Workup

  1. additionwas poured onto ice

Sources & evidence

ORD record
ord-2c4c367239604fd79b0cc663e9683aa6
Source dataset
uspto-grants-2004_08
Patent number
US06774132B1

Reaction notes

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