Water → HCID 86600512, compound

HRID 1766394Notes

Reaction equation

HRID 1766394 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][CH:11]=[CH:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:23][CH:24]=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].O>C(#N)C>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]2[CH:24]([CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:14][CH:13]=[CH:12]2)[CH2:23]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 98102Ethyl 4-bromocrotonateHCID 85344558HCID 85344558, compound

Product 1

HCID 86600512HCID 86600512, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-benzylhexa-3,5-dien-1-amine (338 mg, 1.81 mmol) and triethylamine (0.378 mL, 2.72 mmol) in acetonitrile (15 mL) was treated with ethyl 4-bromobut-2-enoate (0.249 mL, 1.81 mmol). The mixture was stirred at room temperature for 72 hours, then heated to reflux for 6 hours. The mixture was cooled to room temperature and treated with water (15 mL), then extracted with ethyl acetate (3×15 mL). The combined organic phases were dried over magnesium sulfate and concentrated to provide a pale yellow oil. The pale yellow oil was purified by radial thin-layer chromatography, eluting with 10% ethyl acetate/hexane, to provide an oil (165 mg, 30%). 1H NMR (300 MHz, CDCl3) δ7.4-7.2 (m, 5H), 5.62 (m, 2H), 4.1-3.9 (m, 2H), 3.6-3.3 (m, 2H), 2.95 (m, 1H), 2.65 (m, 2H), 2.3-2.1 (m, 6H), 1.78 (m, 1H), 1.57 (m, 1H), 1.19 (t, J=7 Hz, 3H). Mass spec (ES+) m/z 300.3 (M+H+, 100%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hours
  3. temperatureThe mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate (3×15 mL)
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. concentrationconcentrated
  7. customto provide a pale yellow oil
  8. customThe pale yellow oil was purified by radial thin-layer chromatography
  9. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-45058a47e14d4b2ba54dc9ba45c2759d
Source dataset
uspto-grants-2007_06
Patent number
US07230022B2

Reaction notes

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