3,3-Dimethylpiperidine → HCID 22914495, compound

HRID 1378193Notes

Reaction equation

HRID 1378193 reaction equation
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]([CH3:23])[CH2:13][C:12]=23)[N:4]=1.[CH3:24][C:25]1([CH3:31])[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]1>CN(C)C=O>[CH3:24][C:25]1([CH3:31])[CH2:30][CH2:29][CH2:28][N:27]([CH2:2][C:3]2[O:7][N:6]=[C:5]([C:8]3[N:9]=[CH:10][N:11]4[C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=5[C:15](=[O:22])[N:14]([CH3:23])[CH2:13][C:12]=34)[N:4]=2)[CH2:26]1

Participants

4

Reactant 2

HCID 709423,3-DimethylpiperidineHCID 229143143-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 22914495HCID 22914495, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.15 g (3.5 mmol) of 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one were stirred at room temperature for 1 hour with 1 g (8.8 mmol) of 3,3-dimethylpiperidine and 10 ml of N,N-dimethylformamide. By evaporation of the reaction mixture and chromatography of the residue on silica gel while eluting with ethyl acetate/ethanol 9/1 there were obtained 1.32 g (92%) of 3-[5-(3,3-dimethylpiperidin-1-yl)methyl-1,2,4-oxadiazol-3-yl]-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 167°-168°, which was converted into the hydrochloride.

Workup

  1. customBy evaporation of the reaction mixture and chromatography of the residue on silica gel
  2. washwhile eluting with ethyl acetate/ethanol 9/1 there

Sources & evidence

ORD record
ord-1bdf515edb224ae1a5b8961a2faa0f56
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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