Benzylethanolamine → (R)-1-(benzyl(2-hydroxyethyl)amino)propan-2-ol

HRID 41220

Reaction equation

[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][C@@H:13]1[CH2:15][O:14]1>>[CH2:1]([N:8]([CH2:9][CH2:10][OH:11])[CH2:15][C@H:13]([OH:14])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 4348Benzylethanolamine

HCID 146261(R)-1,2-Epoxypropane

Product 1

HCID 60013076(R)-1-(benzyl(2-hydroxyethyl)amino)propan-2-olYield 99%

Conditions

Temperature: 150 °C

Procedure

2-(benzylamino)ethanol (207 ml, 1454.97 mmol) and (R)-2-methyloxirane (153 ml, 2182.46 mmol) were mixed together and pumped at a flow rate of 1 mL/min through a 10 mL loop heated at 150° C. in a flow chemistry system. The back pressure regulator was adjusted in order to achieve a pressure inside the loop of 250 psi. Excess of propylene oxide was removed under vacuum to afford (R)-1-(benzyl(2-hydroxyethyl)amino)propan-2-ol (300 g, 99%) as a colourless liquid. Mass Spectrum: m/z [M+H]+=210.

Workup

customExcess of propylene oxide was removed under vacuum

Sources & evidence

ORD record: ord-56033c54b975422884df9075d3a1ad20
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530470B2

Linked notes

Loading…