Propanal → 1-[2-(dipropylamino)ethyl]-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

HRID 597081Notes

Reaction equation

HRID 597081 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]2[C:9]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:10]=3[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:12][CH2:13][C:7]2=[N:6][N:5]=1.[CH:25](=O)[CH2:26][CH3:27].[C:29]([BH3-])#N.[Na+].[CH2:33](N)[CH2:34]N>O1CCCC1.C(O)(=O)C>[CH2:25]([N:1]([CH2:29][CH2:33][CH3:34])[CH2:2][CH2:3][C:4]1[N:8]2[C:9]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:10]=3[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:12][CH2:13][C:7]2=[N:6][N:5]=1)[CH2:26][CH3:27]

Participants

7

Reactant 4

HCID 527PropanalHCID 3301EthylenediamineHCID 5003444Sodium cyanoborohydrideHCID 126124031-(2-aminoethyl)-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 214489961-[2-(dipropylamino)ethyl]-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

In the manner give in Example 22, a mixture of 1-(2-aminoethyl)-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepin, propionaldehyde and acetic acid in tetrahydrofuran is treated with sodium cyanoborohydride and the resulting boran complex is warmed with aqueous ethylenediamine to give 1-[2-(dipropylamino)ethyl]-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.

Workup

  1. customIn the manner give in Example 22

Sources & evidence

ORD record
ord-a467e3c120734a2faf3028aca7cb8eaa
Source dataset
uspto-grants-1977_03
Patent number
US04012413

Reaction notes

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