Hydrochloric Acid → (+)-9-Chloro-11-[[[2-[2-[(diethylamino)methyl]-piperidin-1-yl]ethyl]amino]carbonyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 2351422Notes

Reaction equation

HRID 2351422 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[NH:7][C:8]3[CH:17]=[CH:16][CH:15]=[N:14][C:9]=3[N:10]([C:11](Cl)=[O:12])[C:4]=2[CH:3]=1.[CH2:21]([N:23]([CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][N:28]1[CH2:33][CH2:34][NH2:35])[CH2:24][CH3:25])[CH3:22].Cl>C(#N)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[NH:7][C:8]3[CH:17]=[CH:16][CH:15]=[N:14][C:9]=3[N:10]([C:11]([NH:35][CH2:34][CH2:33][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH:27]3[CH2:26][N:23]([CH2:21][CH3:22])[CH2:24][CH3:25])=[O:12])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 142099769-Chloro-11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 142100002-[2-[(Diethylamino)methyl]piperidin-1-yl]ethanamine

Product 1

HCID 14210044(+)-9-Chloro-11-[[[2-[2-[(diethylamino)methyl]-piperidin-1-yl]ethyl]amino]carbonyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneYield 33%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared analogously to Example 2 from 9-chloro-11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and (-)-2-[2-[(diethylamino)methyl]-piperidin-1-yl]ethanamine in a yield of 33% of theory. Colourless crystals, m.p. 169°-170° C. (acetonitrile); [α]D20 =-11.92° (dilute hydrochloric acid).

Sources & evidence

ORD record
ord-27e7cebd72b44e469461f484db76de7d
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

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