2-Butene, 1-bromo-3-methyl- → HCID 131718019, compound

HRID 266800Notes

Reaction equation

HRID 266800 reaction equation
[OH:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17][C:15]3=[O:16])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH2:27](Br)[CH:28]=[C:29]([CH3:31])[CH3:30]>C(O)(C)C>[CH2:27]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:9][CH2:10][CH:11]([N:14]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17][C:15]3=[O:16])[CH2:12][CH2:13]2)=[O:7])=[CH:25][CH:26]=1)[CH:28]=[C:29]([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 700922-Butene, 1-bromo-3-methyl-HCID 14969526HCID 14969526, compound

Product 1

HCID 131718019HCID 131718019, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-[1-(4-Hydroxybenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (500 mg), prenyl bromide (0.5 ml) and 1,8-diazabicyclo[5.4.0]-undecene-7 (0.65 ml) are dissolved in isopropanol (10 ml) and the mixture is refluxed with heating for 4 hours. The solvent is distilled off under reduced pressure and the residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=2:1) to give 1-{1-[4-(2-isopentenyloxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (0.159 g).

Workup

  1. temperaturethe mixture is refluxed
  2. temperaturewith heating for 4 hours
  3. distillationThe solvent is distilled off under reduced pressure
  4. customthe residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-d787803ef96744bc9375643778b82eb8
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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