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

HRID 597080Notes

Reaction equation

HRID 597080 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)[CH3:26].C([BH3-])#N.[Na+].[CH2:32](N)[CH2:33]N>C(#N)C.C(O)(=O)C>[CH2:32]([N:1]([CH2:25][CH3:26])[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)[CH3:33]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 3301EthylenediamineHCID 5003444Sodium cyanoborohydrideHCID 126124031-(2-aminoethyl)-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 126124401-[2-(diethylamino)ethyl]-8-chloro-6-phenyl-4H-s-triazolo-[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

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

Sources & evidence

ORD record
ord-70b38c05c52f41c985c03e8ba84dceb2
Source dataset
uspto-grants-1977_03
Patent number
US04012413

Reaction notes

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