4-Chloroisatoic anhydride → 2-amino-4-chloro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

HRID 362918Notes

Reaction equation

HRID 362918 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])OC(=O)[NH:9][C:4]=2[CH:3]=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>CN(C=O)C.CN(C)C1C=CN=CC=1.CCOC(C)=O>[NH2:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:13]=[CH:12][C:5]=1[C:6]([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:11]

Participants

6

Reactant 2

HCID 3291054-Chloroisatoic anhydrideHCID 537860464-Aminomethyl-1-diphenylmethylpiperidine

Product 1

HCID 675946902-amino-4-chloro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-chloro-1,2-dihydro-4H-3,1-benzoxazin-2,4-dione (prepared by cyclization of N-benzyloxycarbonyl-4-chloroanthranilic acid with phosphorus tribromide) (1.0 g, 5.06 mmol) in DMF (18 ml) was added 4-dimethylaminopyridine (62 mg). After 5 mins of agitation at room temperature, 4-aminomethyl-1-diphenylmethylpiperidine (1.56 g, 5.56 mmol) was added to the solution and stirred for 5 hours. The reaction mixture was diluted with AcOEt, washed twice with H2O, dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel to give 2-amino-4-chloro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide, 892 mg (41%): mp 161°-162° C.

Workup

  1. washwashed twice with H2O
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ee29050c2ec643f280fa846aee9ee024
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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