N-bromobutanimide → HCID 57861230, compound

HRID 1518092Notes

Reaction equation

HRID 1518092 reaction equation
[CH3:1][C:2]1[C:3]([N:12]([CH2:19][CH3:20])[CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Br:21]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:1][C:2]1[C:3]([N:12]([CH2:19][CH3:20])[CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57861231HCID 57861231, compound

Product 1

HCID 57861230HCID 57861230, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of N-(3-methylquinoxalin-2-yl)-N-(cyclopentylmethyl)ethylamine (160 mg, 0.59 mmol), N-bromosuccinimide (130 mg, 0.73 mmol), and 2,2′-azobisisobtyronitrile (10 mg) in CCl4 is stirred and refluxed for 1 hour. The reaction mixture is purified by silica gel column chromatography to give N-[3-(bromomethyl)quinoxalin-2-yl]-N-(cyclopentylmethyl)ethylamine. 1H-NMR (400 MHz, CDCl3), δ (ppm): 1.10-1.25 (m, 2H), 1.22 (t, 3H), 1.45-1.73 (m, 8H), 2.22 (m, 1H), 3.42 (d, 2H), 3.49 (q, 2H), 4.73 (s, 2H), 7.51 (ddd, 1H), 7.62 (ddd, 1H), 7.81 (dd, 1H), 7.94 (dd, 1H).

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe reaction mixture is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bc54b1cb20484373be7483ced2ce495d
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

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