Piperidine → HCID 22914453, compound

HRID 1378076Notes

Reaction equation

HRID 1378076 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][C:20]([F:22])=[CH:21][C:16]=4[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=23)[N:4]=1.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CN(C)C=O>[F:22][C:20]1[CH:19]=[CH:18][C:17]2[N:11]3[CH:10]=[N:9][C:8]([C:5]4[N:4]=[C:3]([CH2:2][N:25]5[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]5)[O:7][N:6]=4)=[C:12]3[CH2:13][N:14]([CH3:24])[C:15](=[O:23])[C:16]=2[CH:21]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 22914351HCID 22914351, compound

Product 1

HCID 22914453HCID 22914453, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.04 g (3.0 mmol) of 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]-benzodiazepin-6-one, 0.64 g (7.5 mmol) of piperidine and 10 ml of N,N-dimethylformamide were stirred at room temperature for 4 hours. The reaction mixture was concentrated, the residue was dissolved in methylene chloride and the solution was made alkaline with 4N sodium hydroxide solution. The solution was washed once with saturated sodium chloride solution, dried with magnesium sulfate and evaporated. By chromatography of the residue on silica gel while eluting with methylene chloride/methanol 9/1 there was obtained 0.89 g (75%) of 8-fluoro-5-methyl-3-[5-(piperidin-1-ylmethyl)-1,2,4-oxadiazol-3-yl]-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 182°-4°, which was converted into the hydrochloride of m.p. 254°-6°.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washThe solution was washed once with saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. washBy chromatography of the residue on silica gel while eluting with methylene chloride/methanol 9/1 there

Sources & evidence

ORD record
ord-15a65d9f11cf4545a3413f93bcafe80a
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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