Acetone → 5,11-Dihydro-11-[[2-[3-(dimethylamino)propyl]-1-piperidinyl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 2106675Notes

Reaction equation

HRID 2106675 reaction equation
Cl[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][N:21]([CH3:31])[CH2:22][CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][NH:26]1.CC(C)=O.N>ClCCl.C1CCCCC1.CO.C(OCC)(=O)C>[CH3:31][N:21]([CH3:20])[CH2:22][CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][N:26]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]

Participants

7

Reactant 4

HCID 180AcetoneHCID 222AmmoniaHCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 15057318HCID 15057318, compound

Product 1

HCID 143696265,11-Dihydro-11-[[2-[3-(dimethylamino)propyl]-1-piperidinyl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneYield 51%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 69163855HCID 69163855, compoundSolvent

Procedure

Prepared analogously to Example 4 from 11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 2-[3-(dimethylamino)propyl]piperidine in a yield of 51% of theory. Colourless crystals, m.p. 142°-144° C. (from acetone and ethyl acetate), Rf 0.7 (Macherey-Nagel, Polygram® SIL G/UV254, pre-coated plastic sheets for TLC; eluant: dichloromethane/cyclohexane/methanol/conc. ammonia 68/15/15/2, v/v/v/v)

Sources & evidence

ORD record
ord-ddc32a3088fe48c48cea4a273e5f7d13
Source dataset
uspto-grants-1990_06
Patent number
US04931436

Reaction notes

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