Hydrochloric Acid → (S)-8-chloro-1-(5-dibutylaminomethyl-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 1378207Notes

Reaction equation

HRID 1378207 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:34])[N:9]3[CH2:33][CH2:32][CH2:31][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]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[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:34])[N:9]3[CH2:33][CH2:32][CH2:31][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]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:27][CH2:28][CH2:29][CH3:30])[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54253484(S)-8-chloro-1-(5-dibutylaminomethyl-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 70074864(S)-8-chloro-1-(5-dibutylaminomethyl-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 184.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.01 g (4.16 mmol) of (S)-8-chloro-1-(5-dibutylaminomethyl-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 1.12 ml (4.14 mmol) of 3.70N ethanolic hydrochoric 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 1.99 g (92%) of (S)-8-chloro-1-(5-dibutylaminomethyl-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. 163°-165° and [α]D20 =+23.2° (MeOH, c=1%).

Workup

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

Sources & evidence

ORD record
ord-1ea18b3c23904699bc44c54f12311a5f
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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