Benzylamine → HCID 11781347, compound

HRID 582892Notes

Reaction equation

HRID 582892 reaction equation
[O:1]1[C@H:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C@H:2]1[C:3]([OH:5])=[O:4].P.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH2:15]([NH:22][C@H:2]([C@H:6]([OH:1])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=[O:4])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 14798Sodium Hydroxide2×HCID 24404PhosphineHCID 11805456HCID 11805456, compound

Product 1

HCID 11781347HCID 11781347, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalyst2×HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

To 18,6 g (0.10 mol) of the (2S,3R)-2,3-epoxydecanoic acid (V-2) obtained in (4) above were added 100 ml of water and 150 mg (0.37 mmol) of a phase transfer catalyst "Aliquat 336" (methyltri-n-octylammonium chloride produced by Henckels; hereinafter the same) at room temperature. The mixture was stirred at 2 to 3° C., and 32.1 g (0.30 mol) of benzylamine (VI) was added thereto dropwise, followed by stirring for about 5 minutes. To the mixture was further added 16 ml (0.08 mol) of a 5N sodium hydroxide aqueous solution, followed by refluxing for 2 hours and then stirring at room temperature for 16 hours. The reaction mixture was cooled to 0 to 5° C., 4 ml (0.02 mol) of a 5N sodium hydroxide aqueous solution was added, and the mixture was washed with two 100 ml portions of diisopropyl ether. The aqueous layer was adjusted to pH 5 to 6 by addition of 2N hydrochloric acid aqueous solution while stirring. The precipitated white crystals were washed with water and dried to give 26.7 g (0.091 mol; yield: 91.0%) of the title compound (III) (melting point: 197-199° C.).

Workup

  1. customproduced by Henckels
  2. customat room temperature
  3. stirringby stirring for about 5 minutes
  4. temperatureby refluxing for 2 hours
  5. stirringstirring at room temperature for 16 hours
  6. temperatureThe reaction mixture was cooled to 0 to 5° C.
  7. washthe mixture was washed with two 100 ml portions of diisopropyl ether
  8. additionThe aqueous layer was adjusted to pH 5 to 6 by addition of 2N hydrochloric acid aqueous solution
  9. stirringwhile stirring
  10. washThe precipitated white crystals were washed with water
  11. customdried

Sources & evidence

ORD record
ord-2667e11aaf504dc4a5c42f2c87602181
Source dataset
uspto-grants-1999_07
Patent number
US05925792

Reaction notes

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