N-bromobutanimide → HCID 59807044, compound

HRID 1922369Notes

Reaction equation

HRID 1922369 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)N([Br:25])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CO.C(Cl)Cl>[Br:25][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:8]([CH2:7][CH2:6][N:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[CH2:9][CH2:10][CH2:11]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 59807075HCID 59807075, compound

Product 1

HCID 59807044HCID 59807044, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(2-(pyrrolidin-1-yl)ethyl)-1,2,3,4-tetrahydroquinoline (490 mg, 2.13 mmol) in 10 mL of carbontetrachloride was cooled to 0° C. then treated with NBS (378 mg, 2.13 mmol) portionwise. The resulting suspension was stirred at 0° C. for 3.5 hours. The mixture was filtered through celite and the filter pad was rinsed with 3×20 mL hexanes. The filtrate was concentrated to give a light brown residue which was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2 to give a light brown oil (380 mg, 57.7%). 1H-NMR (CDCl3) δ: 7.09 (dd, J=2.4, 8.7 Hz, 1H), 7.02 (d, J=2.4 Hz, 1H), 6.46 (d, J=8.7 Hz, 1H), 3.42 (t, J=7.8 Hz, 2H), 3.29 (t, J=5.7 Hz, 2H), 2.76-2.55 (m, 8H), 1.95-1.89 (m, 2H), 1.82-1.77 (m, 4H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe filter pad was rinsed with 3×20 mL hexanes
  3. concentrationThe filtrate was concentrated
  4. customto give a light brown residue which

Sources & evidence

ORD record
ord-89c8a7a4d27047fd9d1781fc797876c7
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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