Formaldehyde → 11-[4-[2-[(Diethylamino)methyl]-1-piperidinyl]but-2-ynyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 1084701Notes

Reaction equation

HRID 1084701 reaction equation
[CH2:1]([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)[C:2]#[CH:3].[CH2:20]=O.[CH2:22]([N:24]([CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]1)[CH2:25][CH3:26])[CH3:23]>>[CH2:22]([N:24]([CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][N:29]1[CH2:20][C:3]#[C:2][CH2:1][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)[CH2:25][CH3:26])[CH3:23]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 254287N,N-Diethyl-2-piperidinemethanamineHCID 145520855,11-dihydro-11-(2-propynyl)-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 1455208711-[4-[2-[(Diethylamino)methyl]-1-piperidinyl]but-2-ynyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneYield 28%

Procedure

Prepared analogously to Example (1b) from 5,11-dihydro-11-(prop-2-ynyl)-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, paraformaldehyde and 2-[(diethylamino)methyl]piperidine in a yield of 28% of theory. Colourless crystals, m.p. 132°-134° C.

Sources & evidence

ORD record
ord-abd30d24bc32439e8de700030b57f3b1
Source dataset
uspto-grants-1991_04
Patent number
US05006522

Reaction notes

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