1-Propanesulfonyl chloride → 6-Bromo-1-(propylsulfonyl)-1,2,3,4-tetrahydroquinoline

HRID 2353467Notes

Reaction equation

HRID 2353467 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.[CH2:12]([S:15](Cl)(=[O:17])=[O:16])[CH2:13][CH3:14]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:15]([CH2:12][CH2:13][CH3:14])(=[O:17])=[O:16])[CH2:7][CH2:6][CH2:5]2

Participants

3

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 47150296-Bromo-1,2,3,4-tetrahydroquinoline

Product 1

HCID 684268486-Bromo-1-(propylsulfonyl)-1,2,3,4-tetrahydroquinolineYield 43.2%

Procedure

This compound was prepared according to the general procedure for sulfonylation of indolines and tetrahydroquinolines described in Example 4 using 6-bromo-1,2,3,4-tetrahydroquinoline (0.40 g, 1.89 mmol) and propanesulfonyl chloride (0.31 mL, 2.8 mmol) to provide 6-bromo-1-(propylsulfonyl)-1,2,3,4-tetrahydroquinoline (0.26 g). MS (ES) m/z 317.6; HPLC purity 100.0% at 210-370 nm, 10.2 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammonium formate buffer pH=3.5 acetonitrile+MeOH) for 10 minutes, hold 4 minutes.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-1b516ccc222049b682870b206e386734
Source dataset
uspto-grants-2010_07
Patent number
US07750038B2

Reaction notes

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