Diisopropylethylamine → 3-cyano-N-[2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-1-naphthamide

HRID 749443Notes

Reaction equation

HRID 749443 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH:13]=[CH2:14])[CH2:9][NH:10][CH3:11])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:24]([C:26]1[CH:27]=[C:28]([C:36](Cl)=[O:37])[C:29]2[C:34]([CH:35]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2)#[N:25]>C(Cl)Cl>[C:24]([C:26]1[CH:27]=[C:28]([C:36]([N:10]([CH2:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:12][CH:13]=[CH2:14])[CH3:11])=[O:37])[C:29]2[C:34]([CH:35]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2)#[N:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 18354439[2-(4-Fluorophenyl)pent-4-en-1-yl]methylamineHCID 226366863-Cyano-1-naphthoyl chloride

Product 1

HCID 689791393-cyano-N-[2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-1-naphthamideYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-(4-Fluorophenyl)pent-4-en-1-yl]methylamine (1.0 g, 5.2 mmol) was dissolved in CH2Cl2 and stirred at 0° C. during addition of DIPEA (1.5 g, 11.4 mmol) and 3-cyano-1-naphthoyl chloride (Method 11; 1.1 g, 5.17 mmol). The mixture was stirred with cooling for a short while and then stirred at room temperature for 2 h. The mixture was washed twice with water, once with an aqueous solution of KHSO4, and then with brine. The solvent was removed by evaporation and the residue flash chromatographed on silica gel (methanol-CH2Cl2, 5:95). There was obtained 1.55 g (80%) of 3-cyano-N-[2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-1-naphthamide as an oil. 1H NMR (400 MHz, CDCl3): 2.1-4.9 (cm, 8H), 5.0-5.1 (m, 2H), 5.6-5.8 (m, 1H), 6.4-8.0 (cm, 9H), 8.2 (s, 1H).

Workup

  1. temperaturewith cooling for a short while
  2. stirringstirred at room temperature for 2 h
  3. washThe mixture was washed twice with water, once with an aqueous solution of KHSO4
  4. customThe solvent was removed by evaporation
  5. customthe residue flash chromatographed on silica gel (methanol-CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-a94af863343a4d73b946eeb1319dfab3
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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