Dibenzylamine → Ethanol, 2-[bis(phenylmethyl)amino]-

HRID 1430327Notes

Reaction equation

[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](OCC)(=[O:18])[CH3:17]>[I-].C([N+](CC)(CC)CC)C>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:17][CH2:16][OH:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 140 °C

Procedure

0.5 gram of dibenzylamine (2.5 mmol), 0.446 gram of ethylenecarbonate (5 mmol) and 0.215 gram of tetraethylammoniumiodide (083 mmol) were mixed together at room temperature. The solid mixture was then heated at 140° C. and the resulting suspension was stirred at this temperature for 26 hours. The reaction mixture was diluted with ethyl acetate and extracted with 10 mL of a 0.5M solution of sodium hydroxide. The aqueous phase was washed with ethyl acetate and the combined organic phases were washed twice with brine. The organic phase was dried on magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash chromatography on silica gel (eluant: ethylacetate/hexane 1/2) to afford 0.5 gram of N,N-dibenzyl-2-aminoethanol (yield: 83%) as an oil.

Workup

extractionextracted with 10 mL of a 0.5M solution of sodium hydroxide
washThe aqueous phase was washed with ethyl acetate
washthe combined organic phases were washed twice with brine
customThe organic phase was dried on magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
custompurified by flash chromatography on silica gel (eluant: ethylacetate/hexane 1/2)

Sources & evidence

ORD record: ord-b2572c96332144df8b890297cccd9518
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940782B2

Reaction notes

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