Benzyl Bromide → 1-Benzyl-5-(octyloxy)pyrrolidin-2-one

HRID 1639042Notes

Reaction equation

HRID 1639042 reaction equation
[CH2:1]([O:9][CH:10]1[NH:14][C:13](=[O:15])[CH2:12][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:18]([N:14]1[CH:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:11][CH2:12][C:13]1=[O:15])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 15696565HCID 15696565, compound

Product 1

HCID 30779651-Benzyl-5-(octyloxy)pyrrolidin-2-oneYield 70.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2 g of 5-n-octyloxy-pyrrolidin-2-one, 0.65 g of potassium hydroxide at 85% and 0.2 g of tetra-n-butylammonium bromide in 40 cm3 of tetrahydrofuran, there is added a solution of 1.6 g of benzyl bromide in 5 cm3 of tetrahydrofuran, without exceeding 30° C. After agitating for 2 hours at ambient temperature, filtering and evaporating to dryness, the residue is chromatographed on alumina, (eluent: ethyl acetate--cyclo-hexane, 1--1), and 2 g of the expected product is obtained.

Workup

  1. customwithout exceeding 30° C
  2. filtrationfiltering
  3. customevaporating to dryness
  4. customthe residue is chromatographed on alumina, (eluent: ethyl acetate--cyclo-hexane, 1--1),

Sources & evidence

ORD record
ord-94007ebbc3d94fb99e2ef904bdaa1e76
Source dataset
uspto-grants-1989_11
Patent number
US04882350

Reaction notes

Loading…