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

HRID 2290573Notes

Reaction equation

HRID 2290573 reaction equation
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.CN(C)CCN(C)C.Cl[CH2:30][CH2:31][CH2:32][C:33]1[N:37]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([Br:45])=[CH:41][CH:40]=2)[CH:36]=[N:35][CH:34]=1>O1CCCC1>[Br:45][C:42]1[CH:43]=[CH:44][C:39]([CH:38]2[N:37]3[CH:36]=[N:35][CH:34]=[C:33]3[CH2:32][CH2:31][CH2:30]2)=[CH:40][CH:41]=1

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 2724682Lithium diisopropylamideHCID 148017251-(p-bromobenzyl)-5-(3-chloropropyl)-1H-imidazoleHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium diisopropylamide, 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'-tetramethylethylene diamine and 0.124 g of 5-(3-chloropropyl)-1-p-bromobenzyl-1H-imidazole in 2 ml of tetrahydroduran at -78°. The reaction mixture is stirred for 3.5 hours, quenched at -78° with saturated ammonium chloride solution and extracted with methylene chloride (3×10 ml). The organic extracts are dried over sodium sulfate and evaporated to yield the title compound (c) which is purified by conversion to the hydrochloride salt.

Workup

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

Sources & evidence

ORD record
ord-d4eec199eff8407bbe67f0c9314f7515
Source dataset
uspto-grants-1986_10
Patent number
US04617307

Reaction notes

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