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

HRID 2106690Notes

Reaction equation

HRID 2106690 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].[CH3:20][CH2:21][N:22]([CH2:31][CH3:32])[CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]1>ClCCl.CO>[ClH:1].[CH3:32][CH2:31][N:22]([CH2:21][CH3:20])[CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][N:27]([C:2]([N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[O:15])[NH:7][C:6]3[CH:16]=[CH:17][CH:18]=[N:19][C:5]2=3)=[O:3])[CH2:26]1

Participants

4

Reactant 2

HCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 15057338N,N-Diethyl-2-(3-piperidinyl)-1-ethanamine

Product 1

HCID 703738825,11-Dihydro-11-[[3-[2-(methylethylmethylamino)ethyl]-1-piperidinyl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one-hydrochlorideYield 38%

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-(methylethylmethylamino)ethyl]piperidine in a yield of 38% of theory. Colourless crystals, m.p. 196°-198° C. (D.), Rf 0.21 (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-c78f5315310848f198188f14f96fa599
Source dataset
uspto-grants-1990_06
Patent number
US04931436

Reaction notes

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