Diisopropylamine → 5-(p-Bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

HRID 22549Notes

Reaction equation

HRID 22549 reaction equation
C(NC(C)C)(C)C.[Li].C(NC(C)C)(C)C.C([Li])CCC.CN(C)CCN(C)C.[Br:29][C:30]1[CH:45]=[CH:44][C:33]([CH2:34][N:35]2[C:39]([CH2:40][CH2:41][CH2:42]Cl)=[CH:38][N:37]=[CH:36]2)=[CH:32][CH:31]=1>O1CCCC1>[Br:29][C:30]1[CH:45]=[CH:44][C:33]([CH:34]2[N:35]3[CH:36]=[N:37][CH:38]=[C:39]3[CH2:40][CH2:41][CH2:42]2)=[CH:32][CH:31]=1

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 148017251-(p-bromobenzyl)-5-(3-chloropropyl)-1H-imidazoleHCID 45051747Lithium diisopropylamineHCID 178418339Butyllithium

Product 1

HCID 140971965-(p-Bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium diisopropylamine, prepared at 0° from 0.12 ml of diisopropylamine and 0.33 ml of n-butyllithium (2.5M) in 2 ml of tetrahydrofuran under nitrogen, is added to a solution of 0.13 ml of N,N,N',N'-tetramethyl-ethylenediamine and 0.124 g of 1-(p-bromobenzyl)-5-(3-chloropropyl)-1H-imidazole in 2 ml of tetrahydrofuran at -78°. The reaction mixture is stirred for 3.5 h, quenched at -78° with saturated ammonium chloride solution and extracted with methylene chloride (3×10 ml). The organic extracts and dried over sodium sulfate and evaporated to yield the title compound which is purified by conversion to the hydrochloride salt, m.p. 216°.

Workup

  1. customquenched at -78° with saturated ammonium chloride solution
  2. extractionextracted with methylene chloride (3×10 ml)
  3. dry with materialThe organic extracts and dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-05547cde43b840bd955119d96c0d7e60
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Reaction notes

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