Benzyl Bromide → HCID 20155317, compound

HRID 2413713Notes

Reaction equation

HRID 2413713 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]2[C:9]=1[N:10]=[C:11]1[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]1.C(N(C(C)C)CC)(C)C.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[CH2:26]([N:5]1[CH2:6][CH2:7][C:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:10][C:9]=2[CH:3]([CH2:2][OH:1])[CH2:4]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 20155350HCID 20155350, compound

Product 1

HCID 20155317HCID 20155317, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of 7 g (0.0324 mol) of 5-hydroxymethylazepino[4,5-b]indole, of 5.02 g (0.0388 mol) of diisopropylethylamine, and of 6.67 g (0.0388 mol) of benzyl bromide in 150 ml of chloroform is heated under reflux for 10 hours. The reaction mixture is then drowned in water and alkalified with a saturated aqueous solution of potassium carbonate. The organic phase is separated off and the aqueous phase is again extracted twice with 100 ml portions of chloroform. The organic phases are combined, washed with water, dried over magnesium sulphate, filtered and evaporated to dryness under vacuum. The residue, recrystallized from ether, yields 7.7 g of product.

Workup

  1. temperatureunder reflux for 10 hours
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is again extracted twice with 100 ml portions of chloroform
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness under vacuum
  8. customThe residue, recrystallized from ether

Sources & evidence

ORD record
ord-f8f5bd0c8d2e4b16860ee004aaacda87
Source dataset
uspto-grants-1988_01
Patent number
US04719208

Reaction notes

Loading…