Benzyl Bromide → 1,3-Dibenzylpiperidin-4-one

HRID 396326Notes

Reaction equation

HRID 396326 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 192201-Benzyl-4-piperidoneHCID 24758Sodium hydride

Product 1

HCID 230036591,3-Dibenzylpiperidin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzylpiperidin-4-one (10 g, 53.0 mmole) was added to the stirred suspension of sodium hydride (1.8 g, 53.0 mmole) in tetrahydrofuran (50 ml) at 10° C. The reaction mixture was stirred for 15 min, benzyl bromide (9.0 g, 53.0 mmole) was added at 10° C. The resulting mixture stirred at room temperature for 4 hr and concentrated to dryness. The residue was triturated with water, extracted with ethyl acetate, dried (Na2SO4) and concentrated to give crude product, which was purified through column chromatography. Elute from 10% ethyl acetate in hexane afforded 1,3-dibenzylpiperidin-4-one. Yield 1.8 g (13%), C19H21NO, m/z 280 (M+1), PMR (CDCl3): 2.22-2.62 (4H, m, H2 & H6), 2.86 (2H, m, H5), 3.2 (1H, dd, H3, j=12 Hz), 3.45 (2H, m, CH2Ar), 3.68 (2H, m, N—CH2Ar), 7.1-7.4 (10, m, ArH).

Workup

  1. stirringThe resulting mixture stirred at room temperature for 4 hr
  2. concentrationconcentrated to dryness
  3. customThe residue was triturated with water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give crude product, which
  8. customwas purified through column chromatography
  9. washElute from 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-60f633d5e56f444e8fa368547b3ac9a3
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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