Benzylamine → HCID 54469074, compound

HRID 582901Notes

Reaction equation

HRID 582901 reaction equation
[O:1]1[C@H:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C@H:2]1[C:3]([OH:5])=[O:4].O1[C@H](CC)[C@H]1C(O)=O.[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH2:30]([NH:37][C@H:2]([C@H:6]([OH:1])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:3]([OH:5])=[O:4])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 14798Sodium Hydroxide2×HCID 55299097HCID 55299097, compoundHCID 57039489HCID 57039489, compound

Product 1

HCID 54469074HCID 54469074, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

To 44.7 g (0.15 mol) of the (2S,3R)-2,3-epoxyoctadecanoic acid (V-2) obtained in (4) above were added 150 ml of water and 1.6 g (4 mmol) of a phase transfer catalyst Aliquat 336 at room temperature, followed by stirring at 2 to 3° C. To the mixture was added dropwise 48.2 g (0.45 mol) of benzylamine (VI), followed by further stirring for about 5 minutes. To the mixture was added 24.0 ml (0.12 mol) of a 5N sodium hydroxide aqueous solution, and the mixture was refluxed for 2 hours and then stirred at room temperature for 16 hours. The reaction mixture was cooled to 0 to 5° C., 6.0 ml (0.03 mol) of a 5N sodium hydroxide aqueous solution was added thereto, and the mixture was extracted with 800 ml of diisopropyl ether. The aqueous layer was adjusted to pH 5 to 6 with 2N hydrochloric acid aqueous solution, and the precipitated white crystals were extracted with 1600 ml of diisopropyl ether and collected by filtration under ice-cooling to obtain 55.3 g (0.137 mol; yield: 91.0%) of the title compound (melting point: 132° C.).

Workup

  1. stirringby further stirring for about 5 minutes
  2. temperaturethe mixture was refluxed for 2 hours
  3. stirringstirred at room temperature for 16 hours
  4. temperatureThe reaction mixture was cooled to 0 to 5° C.
  5. extractionthe mixture was extracted with 800 ml of diisopropyl ether
  6. extractionthe precipitated white crystals were extracted with 1600 ml of diisopropyl ether
  7. filtrationcollected by filtration under ice-
  8. temperaturecooling

Sources & evidence

ORD record
ord-3f371e2d226e4ff18fa45a68cb5daf2d
Source dataset
uspto-grants-1999_07
Patent number
US05925792

Reaction notes

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