6-hydroxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione → 2-amino-5-hydroxy-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

HRID 362915Notes

Reaction equation

HRID 362915 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10]C(=O)O[C:7](=[O:12])[C:6]=2[CH:13]=1.[NH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1>CS(C)=O.CCOC(C)=O>[NH2:10][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:13][C:6]=1[C:7]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:18][CH2:17]1)=[O:12]

Participants

5

Reactant 2

HCID 27593156-hydroxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneHCID 537860464-Aminomethyl-1-diphenylmethylpiperidine

Product 1

HCID 675961872-amino-5-hydroxy-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step 2): A mixture of 6-hydroxy-1,2-dihydro-4H-3,1-benzoxazin-2,4-dione (360 mg, 2 mmol) and 4-aminomethyl-1-diphenylmethylpiperidine (420 mg, 1.5 mmol) in DMSO (5 ml) was stirred for 3 hours at room temperature. The reaction mixture was diluted with AcOEt and washed twice with brine. The organic layer was dried over MgSO4 and evaporated, and then the residue was purified by column chromatography on silica gel to give 2-amino-5-hydroxy-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide, 520 mg (63%).

Workup

  1. washwashed twice with brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated
  4. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1efd2246d66a4ed4afc71f9ff590fe47
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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