1,2,3,4-Tetrahydroquinoline → HCID 57475147, compound

HRID 1095528Notes

Reaction equation

HRID 1095528 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Br[CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1>C(Cl)(Cl)Cl>[NH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([CH2:13][CH2:12][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)=[CH:15]1

Participants

4

Reactant 2

HCID 694601,2,3,4-TetrahydroquinolineHCID 769243-(2-Bromoethyl)indole

Product 1

HCID 57475147HCID 57475147, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1,2,3,4-Tetrahydroquinoline (5.94 g, 5.6 ml, 44.6 mmol) was added to a solution of 3-(2-bromoethyl)-indole (5.00 g, 22.3 mmol) in dry chloroform (25 ml) at room temperature and the mixture was then stirred under reflux for 5 h. The reaction mixture cooled overnight. The organic phase was extracted with dil. sulfuric acid (2×50 ml). The aqueous phase was rendered basic with 5N NaOH, while cooling with ice, and extracted with ether (3×50 ml). The organic phase was dried over Na2SO4 and concentrated i. vac. Yield: 5.35 g (Ind-62, 88%)

Workup

  1. temperatureunder reflux for 5 h
  2. temperatureThe reaction mixture cooled overnight
  3. extractionThe organic phase was extracted with dil. sulfuric acid (2×50 ml)
  4. temperaturewhile cooling with ice
  5. extractionextracted with ether (3×50 ml)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated i

Sources & evidence

ORD record
ord-c4b4272cbb974eebb378fcde3533143f
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…