Dipropylamine → HCID 22914513, compound

HRID 1378231Notes

Reaction equation

HRID 1378231 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]4[N:19]=[C:18]([CH2:20]Cl)[O:17][N:16]=4)=[C:10]3[CH2:9][N:8]([CH3:22])[C:7](=[O:23])[C:6]=2[CH:24]=1.[CH2:25]([NH:28][CH2:29][CH2:30][CH3:31])[CH2:26][CH3:27]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]4[N:19]=[C:18]([CH2:20][N:28]([CH2:29][CH2:30][CH3:31])[CH2:25][CH2:26][CH3:27])[O:17][N:16]=4)=[C:10]3[CH2:9][N:8]([CH3:22])[C:7](=[O:23])[C:6]=2[CH:24]=1

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 22914400HCID 22914400, compound

Product 1

HCID 22914513HCID 22914513, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 370 mg (1.01 mmol) of 8-chloro-3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 5 ml of N,N-dimethylformamide was treated with 0.42 ml (3.03 mmol) of dipropylamine and stirred at room temperature under argon for 2 hrs. The solution was evaporated and the residue was triturated in 10 ml of water. The white crystals were filtered off. The product was chromatographed on 20 g of silica gel (ethyl acetate/hexane 1:1, then ethyl acetate). There were obtained 259 mg of 8-chloro-3-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, which was converted with ethereal hydrochloric acid into the hydrochloride. By recrystallization from acetonitrile there were obtained 268 mg (54%) of 8-chloro-1-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one hydrochloride (1:1.6) of m.p. 180°-192° (dec.).

Workup

  1. customThe solution was evaporated
  2. customthe residue was triturated in 10 ml of water
  3. filtrationThe white crystals were filtered off
  4. customThe product was chromatographed on 20 g of silica gel (ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-684efd211fbf440489e9f9908e40d930
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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