Triethylamine → 190515-96-9

HRID 379092Notes

Reaction equation

HRID 379092 reaction equation
O.Cl.[O:3]=[C:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Br[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].C([O-])([O-])=O.[K+].[K+].CCN(CC)CC>CC(C)=O>[O:3]=[C:4]1[CH2:9][CH2:8][N:7]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 76934Methyl 3-bromopropanoateHCID 2723901Piperonylamine

Product 1

HCID 18187970190515-96-9Yield 42%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 4-oxopiperidine hydrochloride monohydrate (10.0 g, 65.1 mmol) and methyl 3-bromopropanoate (7.8 ml, 71.6 mmol) in acetone (100 ml) was added K2CO3 (9.9 g, 71.6 mmol) and Et3N (9.1 ml, 65.3 mmol). The mixture was refluxed for 24 hours. The solid was removed by filtration and the solvent was evaporated. The residue was partitioned between EtOAc and H2O. The organic extracts were combined and dried over Na2SO4. The solvent was evaporated to give the title compound (15.0 g, 27.0 mmol, 42%) as an oil. 1H NMR (300 MHz, CDCI) δ 3.70 (s, 3H), 2.75-2.85 (mult, 6H), 2.52-2.57 (mult, 2H), 2.42-2.46 (mult, 4H).

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customThe solid was removed by filtration
  3. customthe solvent was evaporated
  4. customThe residue was partitioned between EtOAc and H2O
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-bae778c2af4040f99eed4339b68dca3e
Source dataset
uspto-grants-2001_10
Patent number
US06297260B1

Reaction notes

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