Ammonia → 4,9-Dihydro-3-methyl-4-[6-[4-(2-phenyl-ethyl)-1-piperazinyl]-hex-4-ynyl]-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 1084717Notes

Reaction equation

HRID 1084717 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][CH2:29][N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.N.C(OCC)(=O)C.CO.[CH2:46]1[CH2:51]CCC[CH2:47]1>[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:47]#[C:46][CH2:51][N:33]3[CH2:32][CH2:31][N:30]([CH2:29][CH2:28][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:35][CH2:34]3)[C:6]=12

Participants

8

Reactant 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 792141-PhenethylpiperazineHCID 200624924,9-Dihydro-3-methyl-4-(prop-2-ynyl)-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneHCID 22064753Cyclohexane ethyl acetate methanol

Product 1

HCID 200625434,9-Dihydro-3-methyl-4-[6-[4-(2-phenyl-ethyl)-1-piperazinyl]-hex-4-ynyl]-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneYield 17%

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-(2-phenylethyl)piperazine in the presence of catalytic quantities of copper(I)chloride in a yield of 17% of theory. The colourless monohydrochloride melted at 223°-225° C. with decomposition; RF 0.8 (Merck, ready-made TLC plates, silica gel 60 F-254; eluant: ethyl acetate/methanol/cyclohexane/conc. ammonia 8/1/1/0.1 v/v/v/v).

Sources & evidence

ORD record
ord-7057080836774012b62225215464dbb9
Source dataset
uspto-grants-1991_04
Patent number
US05006522

Reaction notes

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