Salicylamide → 1'-benzylspiro[1,3-benzoxazine-2,4'-piperidin]-4(3H)-one

HRID 2036098

Reaction equation

HRID 2036098 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:11]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:11]([N:18]1[CH2:23][CH2:22][C:21]2([NH:10][C:1](=[O:9])[C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=3[O:4]2)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 5147SalicylamideHCID 192201-Benzyl-4-piperidoneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 3798711'-benzylspiro[1,3-benzoxazine-2,4'-piperidin]-4(3H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Salicylamide (7.24 g), 1-benzylpiperidin-4-one (10.0 g) and p-toluenesulfonic acid hydrate (500 mg) were suspended in toluene (200 mL), and the suspension was stirred under reflux overnight while removing the water in the reaction system using a Dean-Stark tube. The mixture was cooled to room temperature, and the resulting precipitate was collected by filtration and washed with water, ethanol and diethyl ether to give 1′-benzylspiro[1,3-benzoxazine-2,4′-piperidin]-4(3H)-one as a crude product (9.7 g). The obtained crude 1′-benzylspiro[1,3-benzoxazine-2,4′-piperidin]-4(3H)-one (5.0 g) and 10% palladium-carbon (1.0 g) were suspended in ethanol (50 mL), and the suspension was stirred at 50° C. for 5 hr under a hydrogen atmosphere. The catalyst was removed by filtration through celite and the solvent was evaporated under reduced pressure. The resulting precipitate was collected by filtration, and washed with ethanol and diethyl ether to give the object product (2.7 g, 77%).

Workup

  1. temperatureunder reflux overnight
  2. customwhile removing the water in the reaction system
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with water, ethanol and diethyl ether

Sources & evidence

ORD record
ord-afa3ae8ba5054595999672db83fd1ed5
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Linked notes

Loading…