Sodium Hydroxide → 1-(4-Chlorobutyl)-1,5,6,7-tetrahydroindol-4-one

HRID 1907831Notes

Reaction equation

HRID 1907831 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[O:10])[C:4]=2[CH:3]=[CH:2]1.[OH-].[Na+].Br[CH2:14][CH2:15][CH2:16][CH2:17][Cl:18].C(OCC)(=O)C.ClCCl>CS(C)=O>[Cl:18][CH2:17][CH2:16][CH2:15][CH2:14][N:1]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[O:10])[C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 813641-Bromo-4-chlorobutaneHCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 235028891-(4-Chlorobutyl)-1,5,6,7-tetrahydroindol-4-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1,5,6,7-tetrahydroindol-4-one (10.0 g) in DMSO (100 mL) was added powdered sodium hydroxide (3.26 g) and the mixture was stirred at ambient temperature for 0.25 hours. 1-Bromo-4-chlorobutane (9.38 mL) was then added and the resulting mixture stirred at ambient temperature for 7 hours after which time TLC (ethyl acetate:dichloromethane 1:1) showed complete reaction. The reaction was poured into ice cold water (250 mL) and stirred for 0.5 hours. An oil separated and was isolated with a separatory funnel. The aqueous layer was extracted with dichloromethane (50 mL). The oil was dissolved with dichloromethane (25 mL) and the combined organics were dried with sodium sulfate, filtered and the solvent removed under vacuum. Flash chromatography (ethyl acetate:hexane, 1:1 to 2:1) yielded an oil (6.0 g) as the titled compound.

Workup

  1. customreaction
  2. stirringstirred for 0.5 hours
  3. customAn oil separated
  4. customwas isolated with a separatory funnel
  5. extractionThe aqueous layer was extracted with dichloromethane (50 mL)
  6. dissolutionThe oil was dissolved with dichloromethane (25 mL)
  7. dry with materialthe combined organics were dried with sodium sulfate
  8. filtrationfiltered
  9. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-f64141ad58624bd1a410e6edf51b335f
Source dataset
uspto-grants-2013_12
Patent number
US08598180B2

Reaction notes

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