Formaldehyde → 4,9-Dihydro-3-methyl-4-[6-[4-(phenylmethyl)-1-piperazinyl]-hex-4-ynyl]-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 1084716Notes

Reaction equation

HRID 1084716 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]([CH2:17][C:18]#[CH:19])[C:6]=12.C=O.[C:22]1([CH2:28][N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH:35](OC(C)C)([CH3:37])[CH3:36].C(#N)C>[Cu]Cl>[CH3:1][C:2]1[S:3][CH:4]=[C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]([CH2:17][CH2:18][CH2:19][C:36]#[C:35][CH2:37][N:32]3[CH2:31][CH2:30][N:29]([CH2:28][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:34][CH2:33]3)[C:6]=12

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 759941-BenzylpiperazineHCID 200624924,9-Dihydro-3-methyl-4-(prop-2-ynyl)-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneHCID 22714958Acetonitrile diisopropyl ether

Product 1

HCID 200625344,9-Dihydro-3-methyl-4-[6-[4-(phenylmethyl)-1-piperazinyl]-hex-4-ynyl]-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneYield 12%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

Prepared analogously to Example lb) from 4,9-dihydro-3-methyl-4-(prop-2-ynyl)-10H-thieno[3,4-b][1,5]benzodiazepin-10-one, paraformaldehyde and N-(phenylmethyl)piperazine in the presence of copper(I)chloride in a yield of 12% of theory. RF 0.5 (Merck, readymade TLC plates, silica gel 60F-254; eluant: dichloromethane/ethanol 9/1 v/v).

Sources & evidence

ORD record
ord-cfff08fbf1b74b639f2c477791b62f99
Source dataset
uspto-grants-1991_04
Patent number
US05006522

Reaction notes

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