Acetonitrile → 1-benzyl-2,3-dihydro-1H-imidazo[1,2-a]pyridinium bromide

HRID 261114Notes

Reaction equation

HRID 261114 reaction equation
[N:1]1[CH2:2][CH2:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(#N)C.[Br:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)C>[Br-:13].[CH2:14]([NH+:1]1[C:5]2=[CH:6][CH:7]=[CH:8][CH2:9][N:4]2[CH2:3][CH2:2]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 23423819HCID 23423819, compound

Product 1

HCID 867350121-benzyl-2,3-dihydro-1H-imidazo[1,2-a]pyridinium bromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 2.0 g. of 2,3-dihydroimidazo[1,2-a]pyridine in 40 ml. of dry acetonitrile is added 3.42 g. of α-bromotoluene and the resulting mixture heated to reflux overnight. The solution is cooled to room temperature and treated with 30 ml. of diethyl ether. The precipitated solid is filtered and recrystallized from acetonitrile, 1.64 g., m.p. 143°-145° C.

Workup

  1. temperatureto reflux overnight
  2. additiontreated with 30 ml
  3. filtrationThe precipitated solid is filtered
  4. customrecrystallized from acetonitrile, 1.64 g

Sources & evidence

ORD record
ord-ccce14f92fcb4fe8b8277afd9c43c742
Source dataset
uspto-grants-1979_08
Patent number
US04163745

Reaction notes

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