Hydrochloric Acid → (S)-8-chloro-1-(5-diethylaminomethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one hydrochloride

HRID 1378203Notes

Reaction equation

HRID 1378203 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:30])[N:9]3[CH2:29][CH2:28][CH2:27][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19]([CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[C:7]2[C:8](=[O:30])[N:9]3[CH2:29][CH2:28][CH2:27][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19]([CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22876632(S)-8-chloro-1-(5-diethylaminomethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo-[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

Product 1

HCID 70076595(S)-8-chloro-1-(5-diethylaminomethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one hydrochlorideYield 154.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.84 g (1.96 mmol) of (S)-8-chloro-1-(5-diethylaminomethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one in 10 ml of ethanol was treated with 0.41 ml (1.96 mmol) of 4.78N ethanolic hydrochloric acid. After stirring at room temperature for 10 minutes the solution obtained was completely freed from the solvents. The residue was recrystallized from ethanol/ether. There was obtained 0.70 g (77%) of (S)-8-chloro-1-(5-diethylaminomethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one hydrochloride (1:1) as white crystals; m.p. 205°-207° and [α]D20 =+25.2° (MeOH, c=1%).

Workup

  1. customobtained
  2. customThe residue was recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-fa460c41c0514649bd623c2a60fbb764
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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