Phenethyl bromide → MDL 11,939

HRID 1681080Notes

Reaction equation

HRID 1681080 reaction equation
[C:1]1([CH:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]1([CH:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:11][CH2:10]2)[OH:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 339086Phenyl-piperidin-4-yl-methanol

Product 1

HCID 71781MDL 11,939

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of alpha-phenyl-4-piperidinemethanol (1.5 g, 7.8 mmol), 2-bromoethyl benzene (1.1 ml, 8.0 mmol) and potassium carbonate (1.1 g, 8.0 mmol) in dry DMF (20 ml) was heated at 80° C. over the weekend (60 h). The excess DMF was distilled off at reduced pressure and the residue was dissolved in ethyl acetate. The organic phase was washed with H2O (3×100 ml), saturated aqueous NaCl (1×100 ml), dried (MgSO4), filtered and evaporated to give a pale yellow oil which eventually crystallized. After recrystallization from ethyl acetate-hexane, a white crystalline solid was obtained, mp 125°-128° C.

Workup

  1. distillationThe excess DMF was distilled off at reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic phase was washed with H2O (3×100 ml), saturated aqueous NaCl (1×100 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a pale yellow oil which
  8. customeventually crystallized
  9. customAfter recrystallization from ethyl acetate-hexane
  10. customa white crystalline solid was obtained

Sources & evidence

ORD record
ord-f0286529424a4436a8792a70a83617ab
Source dataset
uspto-grants-1992_12
Patent number
US05169096

Reaction notes

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