Hydrochloric Acid → 7-chloro-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 hydrochloride

HRID 1378219Notes

Reaction equation

HRID 1378219 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:29])[N:9]([CH3:28])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19]([CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[F:30].Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[C:7]2[C:8](=[O:29])[N:9]([CH3:28])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19]([CH2:21][N:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]4)[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[F:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22914252HCID 22914252, compound

Product 1

HCID 229142517-chloro-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 hydrochlorideYield 175%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.37 g (3.18 mmol) of 7-chloro-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 were dissolved in 50 ml of hot ethanol and treated at 40° with 0.95 ml (3.5 mol) of 3.7N ethanolic hydrochloric acid. After stirring at 0° for 30 minutes the solution was concentrated to a volume of ~20 ml and treated with 100 ml of ether. The white suspension obtained was suction filtered. There were obtained 1.30 g (88%) of 7-chloro-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 hydrochloride (1:1) as white crystals; m.p. 240°-243° (dec.).

Workup

  1. concentrationwas concentrated to a volume of ~20 ml
  2. additiontreated with 100 ml of ether
  3. customThe white suspension obtained
  4. filtrationfiltered

Sources & evidence

ORD record
ord-e7e013bec5f44ba784bb094d080c931d
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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