N-(2-Hydroxyethyl)aniline → HCID 68576987, compound
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C@H:6]2[O:8][CH2:7]2)=[CH:4][CH:3]=1.[NH:11]([CH2:18][CH2:19][OH:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C@@H:6]([OH:8])[CH2:7][N:11]([CH2:18][CH2:19][OH:20])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1Participants
3
Conditions
- Temperature
- 60 °C
Procedure
To (R)-4-chloro-styrene oxide (1.55 g, 10.0 mmol), 2-anilinoethanol (1.44 g, 1.05 equivalents) was added; and the mixture was stirred at 60° C. for 15 hours. The mixture was cooled to room temperature to obtain 3.38 of the reaction mixture of the title compound (chemical purity: 52.1 area %, 2-anilinoethanol: 1.5 area %, 28.4 area % of regioisomer was contaminated). The reaction mixture was purified by column chromatography (gel: silica gel, solvent: ethyl acetate/hexane=1/1), and the obtained fractions were concentrated and dried under vacuum, to obtain 1.68 g of the title compound as pale yellow oil (yield: 49%, chemical purity: 91.7 area %; 2-anilinoethanol was not detected; 4.7 area % of regioisomer was contaminated). The retention time in the chemical purity analysis method was 5.6 min.