Pyridine → HCID 86684844, compound

HRID 537838Notes

Reaction equation

HRID 537838 reaction equation
[CH2:1]([CH:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37]C)[OH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].N1C=CC=C[CH:40]=1.O=C(Cl)[O:47][C:48](Cl)(Cl)Cl.[CH3:53][N:54]([CH3:60])[CH2:55][CH2:56][NH:57][CH2:58][CH3:59]>CCOCC>[CH3:53][N:54]([CH3:60])[CH2:55][CH2:56][N:57]([CH2:58][CH3:59])[C:48](=[O:47])[O:20][CH:19]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH3:40])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10426DiphosgeneHCID 671622-EthylaminoethyldimethylamineHCID 44468963Dlin-MeOH

Product 1

HCID 86684844HCID 86684844, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a solution of dilinoleyl methanol (1.0 g, 1.9 mmol) and pyridine (230 μL, 4.7 mmol) in anhydrous ether (10 mL) cooled to −15° C. under nitrogen was slowly added diphosgene (0.38 mL, 3.14 mmol). The reaction was stirred for 1 hour at −15° C., then N,N-dimethyl-N′-ethyl-ethylenediamine (2.2 mL, 14.2 mmol) was added. The solution was warmed to room temperature and stirred for 30 minutes. The solution was diluted with diethyl ether (50 mL) and filtered to remove the urea and ammonium salts. The ether filtrate was concentrated in vacuo to dryness and the residue was purified by column chromatography (100% ethyl acetate) to afford the title compound as a colorless oil (990 mg, 78%). 1H NMR (400 MHz, CDCl3): δ 5.41-5.27 (m, 8H), 4.77-4.69 (m, 1H), 3.55-3.20 (m, 4H), 2.79-2.72 (m, 4H), 2.72-2.56 (m, 1H), 2.55-2.21 (m, 7H), 2.08-1.96 (m, 8H), 1.58-1.44 (m, 4H), 1.39-1.15 (m, 36H), 1.10 (t, J=7.0 Hz, 3H), 0.90-0.82 (m, 6H).

Workup

  1. temperatureThe solution was warmed to room temperature
  2. stirringstirred for 30 minutes
  3. filtrationfiltered
  4. customto remove the urea and ammonium salts
  5. concentrationThe ether filtrate was concentrated in vacuo to dryness
  6. customthe residue was purified by column chromatography (100% ethyl acetate)

Sources & evidence

ORD record
ord-7be61616716549a49cbd210749617c30
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

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