Triethylamine → (4-Cyano-5-methyl-4-(5-cyano-2-thienyl)hexyl]-4-[3-(5-cyano-2-thieny)propyl]piperazine

HRID 1071651Notes

Reaction equation

[C:1]([C:3]([C:11]1[S:12][C:13]([C:16]#[N:17])=[CH:14][CH:15]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6]I)#[N:2].C(N(CC)CC)C.[C:25]([C:27]1[S:31][C:30]([CH2:32][CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[CH:29][CH:28]=1)#[N:26]>C(#N)C>[C:1]([C:3]([C:11]1[S:12][C:13]([C:16]#[N:17])=[CH:14][CH:15]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6][N:38]1[CH2:39][CH2:40][N:35]([CH2:34][CH2:33][CH2:32][C:30]2[S:31][C:27]([C:25]#[N:26])=[CH:28][CH:29]=2)[CH2:36][CH2:37]1)#[N:2]

Participants

Conditions

Temperature: 55 °C

Procedure

In acetonitrile (3 ml) was dissolved 200 mg (0.56 mmol) of 4-cyano-5-methyl-4-(5-cyano-2-thienyl)hexyl iodide. To the mixture were added 78.0 μl (0.56 mmol) of triethylamine and 178 mg (0.76 mmol) of 1-[3-(5-cyano-2-thieny)propyl]piperazine, followed by stirring at 55° C. After 5 hours, the reaction solution was concentrated, and the residue was subjected to Cromatorex NH silica gel (ethyl acetate/hexane=1/2), to give 243 mg (0.52 mmol, 92.8%) of the title compound as a yellow syrup.

Workup

concentrationthe reaction solution was concentrated

Sources & evidence

ORD record: ord-b8df701236b54878a1e594ae684f4b53
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06906072B1

Reaction notes

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