Pyridine → (6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-18-yl 3-(dimethylamino)propyl(hexyl)carbamate

HRID 537837Notes

Reaction equation

HRID 537837 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.[CH2:53]([NH:59][CH2:60][CH2:61][CH2:62][N:63]([CH3:65])[CH3:64])[CH2:54][CH2:55][CH2:56][CH2:57][CH3:58]>CCOCC.CCOCC.ClCCl>[CH3:64][N:63]([CH3:65])[CH2:62][CH2:61][CH2:60][N:59]([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[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

7

Reactant 4

HCID 1049PyridineHCID 10426DiphosgeneHCID 28878850N-hexyl-N',N'-dimethylpropane-1,3-diamineHCID 44468963Dlin-MeOH

Product 1

HCID 86684848(6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-18-yl 3-(dimethylamino)propyl(hexyl)carbamateYield 78.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 21881112Ethyl ether methylene chlorideSolvent

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 (380 μL, 3.1 mmol). The reaction was stirred for 20 minutes at −15° C., then N-hexyl-N′,N′-dimethylpropane-1,3-diamine (3.8 g, 20.3 mmol) was added as a solution in 4:1 ether/dichloromethane (10 mL). The solution was warmed to room temperature and stirring was continued for 20 minutes. Upon completion, the solution was diluted with diethyl ether (100 mL) and washed with saturated sodium bicarbonate (2×50 mL). The ether extract was dried on magnesium sulphate, filtered, concentrated in vacuo to dryness. The residue was purified by column chromatography (100% ethyl acetate) to afford the title compound as a colorless oil (1.1 g, 76%). 1H NMR (400 MHz, CDCl3): δ 5.43-5.26 (m, 8H), 4.80-4.68 (m, 1H), 3.35-3.15 (m, 4H), 2.81-2.75 (m, 4H), 2.66-2.25 (m, 8H), 2.10-1.70 (m, 14H), 1.64-1.46 (m, 6H), 1.40-1.20 (m, 38H), 1.00-0.93 (m, 3H), 0.92-0.86 (m, 6H).

Workup

  1. temperatureThe solution was warmed to room temperature
  2. stirringstirring
  3. waitwas continued for 20 minutes
  4. washwashed with saturated sodium bicarbonate (2×50 mL)
  5. extractionThe ether extract
  6. customwas dried on magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to dryness
  9. customThe residue was purified by column chromatography (100% ethyl acetate)

Sources & evidence

ORD record
ord-54d244c0f9e34aa59229214964f97422
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

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