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

HRID 2106693Notes

Reaction equation

HRID 2106693 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].[CH:20]1([CH2:25][NH:26][CH2:27][CH2:28][CH:29]2[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]2)[CH2:24][CH2:23][CH2:22][CH2:21]1.C(O)C>ClCCl.CO>[ClH:1].[CH:20]1([CH2:25][NH:26][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]1

Participants

5

Reactant 3

HCID 702EthanolHCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 150573093-[2-[(Cyclopentyl)methylamino]ethyl]piperidine

Product 1

HCID 7037376411-[[3-[2-[(Cyclopentyl)methylamino]ethyl]-1-piperidinyl]carbonyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one-hydrochlorideYield 54%

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-[(cyclopentyl)methylamino]ethyl]piperidine in a yield of 54% of theory. Colourless crystals, m.p. 244°-246° C. (ethanol), Rf 0.31 (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-e63a51d7c7554e4ba3241357eb5c1db3
Source dataset
uspto-grants-1990_06
Patent number
US04931436

Reaction notes

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