Dibutylamine → HCID 22914217, compound

HRID 1378099Notes

Reaction equation

HRID 1378099 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([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:5][N:4]=1.[CH2:24]([NH:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH3:27]>CN(C)C=O>[CH2:24]([N:28]([CH2:2][C:3]1[O:7][C:6]([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:5][N:4]=1)[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 8148DibutylamineHCID 22914464HCID 22914464, compound

Product 1

HCID 22914217HCID 22914217, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.66 g (2 mmol) of 3-(5-chloromethyl-1,3,4-oxadiazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one were stirred at 75° overnight with 1.2 g (9.3 mmol) of dibutylamine and 10 ml of N,N-dimethylformamide. After evaporation of the reaction mixture and chromatography of the residue on silica gel while eluting with ethyl acetate there was obtained 0.72 g (85%) of 3-(5-dibutylaminomethyl-1,3,4-oxadiazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, which was converted into the hydrochloride of m.p. 211°-213°.

Workup

  1. customAfter evaporation of the reaction mixture and chromatography of the residue on silica gel
  2. washwhile eluting with ethyl acetate

Sources & evidence

ORD record
ord-434fb96df97c4a2795fd1e98ddd35795
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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