4-Piperidinebutanamine, N,N-diethyl- → 9-Chloro-11-[[[2-[4-[4-(diethylamino)butyl]-piperidin-l-yl]ethyl]amino]carbonyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 2351455Notes

Reaction equation

HRID 2351455 reaction equation
Br[CH2:2][CH2:3][NH:4][C:5]([N:7]1[C:13]2[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=2[C:11](=[O:19])[NH:10][C:9]2[CH:20]=[CH:21][CH:22]=[N:23][C:8]1=2)=[O:6].[CH2:24]([N:26]([CH2:37][CH3:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[CH3:25]>CN(C)C=O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]2[C:11](=[O:19])[NH:10][C:9]3[CH:20]=[CH:21][CH:22]=[N:23][C:8]=3[N:7]([C:5]([NH:4][CH2:3][CH2:2][N:34]3[CH2:35][CH2:36][CH:31]([CH2:30][CH2:29][CH2:28][CH2:27][N:26]([CH2:37][CH3:38])[CH2:24][CH3:25])[CH2:32][CH2:33]3)=[O:6])[C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 100819184-Piperidinebutanamine, N,N-diethyl-HCID 1984598911-[[[2-bromo-ethyl]amino]carbonyl]-9-chloro-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 536447109-Chloro-11-[[[2-[4-[4-(diethylamino)butyl]-piperidin-l-yl]ethyl]amino]carbonyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 109 from 11-[[[2-bromo-ethyl]amino]carbonyl]-9-chloro-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 4-[4-(diethylamino)butyl]piperidine, but using dimethylformamide instead of acetonitrile, in a yield of 19% of theory. Colourless crystals, m.p. 157° C.

Sources & evidence

ORD record
ord-e1d70b939cfe4d2dbe3915076f2d8b47
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

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