11-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one → 5,11-Dihydro-11-[[3-[2-(hexahydro-1H-1-azepinyl)ethyl]-1-piperidinyl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one-hydrochloride

HRID 2106694Notes

Reaction equation

HRID 2106694 reaction equation
[Cl:1][C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[CH:17][CH:18]=[N:19][C:5]1=2)=[O:3].[N:20]1([CH2:27][CH2:28][CH:29]2[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(O)C.O.CC(C)=O>ClCCl.CO>[ClH:1].[N:20]1([CH2:27][CH2:28][CH:29]2[CH2:34][CH2:33][CH2:32][N:31]([C:2]([N:4]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[C:8](=[O:15])[NH:7][C:6]4[CH:16]=[CH:17][CH:18]=[N:19][C:5]3=4)=[O:3])[CH2:30]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 150573143-[2-(hexahydro-1H-1-azepinyl)ethyl]piperidineHCID 86654442Ethanol acetone water

Product 1

HCID 143696575,11-Dihydro-11-[[3-[2-(hexahydro-1H-1-azepinyl)ethyl]-1-piperidinyl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one-hydrochlorideYield 78%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent2×

Procedure

Prepared analogously to Example 1 from 11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 3-[2-(hexahydro-1H-1-azepinyl)ethyl]piperidine in a yield of 78% of theory. Colourless crystals, m.p. 255°-257° C. (ethanol/water/acetone 45/5/50, v/v/v), Rf 0.27 (Merck DC ready made TLC plates, silica gel 60 F254 ; eluant: dichloromethane/methanol/conc. ammonia 90/10/1, v/v/v).

Sources & evidence

ORD record
ord-c5ba24020e554c258fc2ba6af49ab0ce
Source dataset
uspto-grants-1990_06
Patent number
US04931436

Reaction notes

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