Hydrochloric Acid → (S)-8-chloro-1-(5-dipropylaminomethyl-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 1378205Notes

Reaction equation

HRID 1378205 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:32])[N:9]3[CH2:31][CH2:30][CH2:29][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]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[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:32])[N:9]3[CH2:31][CH2:30][CH2:29][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]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54427205(S)-8-chloro-1-(5-dipropylaminomethyl-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 70075023(S)-8-chloro-1-(5-dipropylaminomethyl-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 136.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.93 g (4.24 mmol) of (S)-8-chloro-1-(5-dipropylaminomethyl-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 20 ml of ethanol were treated with 0.88 ml (4.2 mmol) 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 were obtained 1.42 g (68%) of (S)-8-chloro-1-(5-dipropylaminomethyl-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. 183°-185° and [α]D20 =+24.4° (MeOH, c=1%).

Workup

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

Sources & evidence

ORD record
ord-48aab673d8ec4162b5fecac58161563d
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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