Triethylamine → Benzyl (4-oxopiperidin-1-yl)acetate

HRID 379085Notes

Reaction equation

HRID 379085 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[C:8]([O:11][CH:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:10])[CH3:9].C([O-])([O-])=O.[K+].[K+].CCN(CC)CC>CC(C)=O>[O:7]=[C:4]1[CH2:5][CH2:6][N:1]([CH2:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 337214-PiperidoneHCID 9991399HCID 9991399, compound

Product 1

HCID 18187989Benzyl (4-oxopiperidin-1-yl)acetateYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of 4-piperidone (10.0 g, 65.0 mmol) and bromobenzyl acetate (14.9 g, 65.2 mmol) in acetone (100 ml) was added K2CO3 (9.0 g) and Et3N (9.1 ml, 65.2 mmol). The reaction mixture was stirred at room temperature for two days, and then the solvent was evaporated. The residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The organic extracts were combined and dried over Na2SO4. The solvent was evaporated to afford the title compound (13.3 g, 53.8 mmol, 83%) as a thick oil. 1H NMR (300 MHz, CDCl3) δ 7.33-7.37 (m, 5H), 5.18 (s, 2H), 3.42 (s, 2H), 2.91 (t, J=6.1 Hz, 4H), 2.50 (t, J=6.1 Hz, 4H).

Workup

  1. customthe solvent was evaporated
  2. customThe residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-935551db6865440b9ffada4c72ee8ce8
Source dataset
uspto-grants-2001_10
Patent number
US06297260B1

Reaction notes

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