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

HRID 1071650Notes

Reaction equation

HRID 1071650 reaction equation
[C:1]([C:3]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[C:16]#[N:17])([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[CH:28]=[C:29]([CH:39]=[CH:40][CH:41]=1)[O:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)#[N:26]>C(#N)C>[C:1]([C:3]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[C:16]#[N:17])([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6][N:36]1[CH2:35][CH2:34][N:33]([CH2:32][CH2:31][O:30][C:29]2[CH:39]=[CH:40][CH:41]=[C:27]([C:25]#[N:26])[CH:28]=2)[CH2:38][CH2:37]1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 223936831-(3-Cyanophenoxyethyl)piperazineHCID 223938264-Cyano-5-methyl-4-(3-cyano-2-thienyl)hexyl iodide

Product 1

HCID 22393576(4-Cyano-5-methyl-4-(3-cyano-2-thienyl)hexyl]-4-[2-(3-cyanophenoxy)ethyl]piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 1.5 ml of acetonitrile was dissolved 111 mg (0.31 mmol) of 4-cyano-5-methyl-4-(3-cyano-2-thienyl)hexyl iodide. To the mixture were added 56.2 μl (0.40 mmol) of triethylamine and 109 mg (0.47 mmol) of 1-(3-cyanophenoxyethyl)piperazine, followed by stirring for 3 days. The organic layer separated by adding ethyl acetate and brine to the reaction solution was dried over magnesium sulfate, and then evaporated, to give a crude product. The crude product was subjected to 12.5 g of Cromatorex NH silica gel (ethyl acetate/hexane-1/2), to give 144 mg (quantitative) of the title compound as a yellow syrup.

Workup

  1. customThe organic layer separated
  2. additionby adding ethyl acetate and brine to the reaction solution
  3. dry with materialwas dried over magnesium sulfate
  4. customevaporated
  5. customto give a crude product

Sources & evidence

ORD record
ord-8c2c141c6ce34d538687ccdb5f8b6e93
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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