Benzocaine → ethyl 4-(4,4-dimethyl-2,6-dioxopiperidin-1-yl)benzoate

HRID 2085693Notes

Reaction equation

HRID 2085693 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][C:14]1([CH3:22])[CH2:20][C:19](=O)[O:18][C:16](=[O:17])[CH2:15]1.C(Cl)(=O)C>ClCCCl.ClCCl>[CH3:13][C:14]1([CH3:22])[CH2:15][C:16](=[O:17])[N:1]([C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[C:19](=[O:18])[CH2:20]1

Participants

6

Reactant 3

HCID 2337BenzocaineHCID 6367Acetyl chlorideHCID 778133,3-Dimethylglutaric anhydride

Product 1

HCID 2826262ethyl 4-(4,4-dimethyl-2,6-dioxopiperidin-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 4-aminobenzoate (1.0 g, 6.1 mmol) and 3,3-dimethylglutaric anhydride (0.95 g, 6.7 mmol) in 1,2-dichloroethane (15 mL) was heated to reflux for 1 hour, cooled to room temperature, and treated dropwise with acetyl chloride (0.88 mL, 12.5 mmol). The mixture was heated to reflux for 1 hour, cooled to room temperature, diluted with dichloromethane, washed sequentially with water, saturated NaHCO3, and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS(DCI(+)) m/e 290 (M+H)+.

Workup

  1. temperatureto reflux for 1 hour
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 1 hour
  4. temperaturecooled to room temperature
  5. washwashed sequentially with water, saturated NaHCO3, and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a45d6fe8e646403faf2a4ad284838a8b
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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