1-Bromo-3-chloropropane → HCID 18995646, compound

HRID 374972Notes

Reaction equation

HRID 374972 reaction equation
[C:1]1([CH2:7][N:8]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]2[C:18]3[N:19]=[C:20]([CH3:26])[N:21]([CH2:22][O:23][CH2:24][CH3:25])[C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.Br[CH2:40][CH2:41][CH2:42][Cl:43].C(OCC)(=O)C>O1CCCC1.C(OCC)C.O>[C:28]1([CH2:27][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:9]2[C:18]3[N:19]=[C:20]([CH2:26][CH2:40][CH2:41][CH2:42][Cl:43])[N:21]([CH2:22][O:23][CH2:24][CH3:25])[C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 8857Ethyl AcetateHCID 18995659HCID 18995659, compoundHCID 178418339Butyllithium

Product 1

HCID 18995646HCID 18995646, compoundYield 57.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, a solution of N,N-bis(phenylmethyl)-1-ethoxymethyl-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.12 g, 2.56 mmole) in tetrahydrofuran (20 mL) was cooled to -78° C. Butyllithium (1.03 mL of 2.5M in hexanes, 2.56 mmole) was added and the reaction mixture was stirred for 5 minutes. 1-Bromo-3-chloropropane (2.7 mL, 25 mmole) was added and the reaction mixture was allowed to warm to ambient temperature. When the reaction was complete, as indicated by thin layer chromatography (silica gel, 30% ethyl acetate in hexanes v/v), the reaction mixture was diluted with diethyl ether and water. The ether layer was separated, dried over magnesium sulfate and then concentrated under vacuum. The resulting residue was purified by column chromatography (silica gel eluting with 10-20% ethyl acetate in hexanes v/v) to provide 0.76 g of N,N-bis(phenylmethyl)-2-(4-chlorobutyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. customThe ether layer was separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe resulting residue was purified by column chromatography (silica gel eluting with 10-20% ethyl acetate in hexanes v/v)

Sources & evidence

ORD record
ord-de9d8d869f8849cb8f876e6b08d08bd9
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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