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

HRID 2106692Notes

Reaction equation

HRID 2106692 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([CH2:25][CH2:26][CH:27]2[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]2)[CH2:24][CH2:23][CH2:22][CH2:21]1>ClCCl.CO>[ClH:1].[N:20]1([CH2:25][CH2:26][CH:27]2[CH2:32][CH2:31][CH2:30][N:29]([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])[CH2:28]2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 150573123-(2-(Pyrrolidin-1-yl)ethyl)piperidine

Product 1

HCID 230487425,11-Dihydro-11-[[3-[2-(1-pyrrolidinyl)ethyl]-1-piperidinyl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one-hydrochlorideYield 58%

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-(1-pyrrolidinyl)ethyl]piperidine in a yield of 58% of theory. Colourless crystals, Rf 0.25 (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-4934248be67b4e569a64976907b24fd3
Source dataset
uspto-grants-1990_06
Patent number
US04931436

Reaction notes

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