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

HRID 2106681Notes

Reaction equation

HRID 2106681 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][CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]2)[CH2:24][CH2:23][CH2:22][CH2:21]1.O.CC(C)=O>O>[ClH:1].[N:20]1([CH2:25][CH2:26][CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][N:30]([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])[CH2:29]2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 150573053-[3-(Pyrrolidin-1-yl)propyl]piperidineHCID 18366337Propan-2-one--water (1/1)

Product 1

HCID 143696405,11-Dihydro-11-[[3-[3-(1-pyrrolidinyl)propyl]-1-piperidinyl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one-hydrochlorideYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared analogously to Example 1 from 11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 3-[3-(1-pyrrolidinyl)propyl]piperidine in a yield of 56% of theory. Colourless crystals, m.p. >260° C. (from water/acetone), water solubility: about 0.3%.

Sources & evidence

ORD record
ord-2765767ce5014e61bcfebad1c61d1721
Source dataset
uspto-grants-1990_06
Patent number
US04931436

Reaction notes

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