1-Bromo-4-chlorobutane → HCID 18995649, compound

HRID 374979Notes

Reaction equation

HRID 374979 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][CH2:43][Cl:44]>O1CCCC1>[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][CH2:43][Cl:44])[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

5

Reactant 3

HCID 813641-Bromo-4-chlorobutaneHCID 18995659HCID 18995659, compoundHCID 178418339Butyllithium

Product 1

HCID 18995649HCID 18995649, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N,N-bis(phenylmethyl)-1-ethoxymethyl-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.5 g, 3.43 mmole, Example 1 Part E) in tetrahydrofuran (30 mL) was cooled to -78° C. Butyllithium (1.4 mL of 2.5M in hexanes, 3.5 mmole) was added dropwise followed by the addition of 1-bromo-4-chlorobutane (4 mL, 34 mmole). The reaction mixture was allowed to warm to ambient temperature then it was quenched 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% ethyl acetate in hexanes v/v) to provide 1.5 g of N,N-bis(phenylmethyl)-2-(5-chloropentyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

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

Sources & evidence

ORD record
ord-a62d8bc8e20f4e6e843ca77f47b9081b
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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