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

HRID 66013Notes

Reaction equation

HRID 66013 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-f6469acff457428c8841e7511c65bfd0
Source dataset
uspto-grants-1978_12
Patent number
US04129567

Reaction notes

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