Ethanol → 1,3-Dimethoxy-2-methylpropan-2-amine

To a 3-necked 3 L RB flask equipped with overhead stirrer, condenser and N2 inlet line was added NaH (Morton Thiokol, Inc. - Alfa Products, 60% in mineral oil, 44 g, 1.1 mol). After washing with hexane (3×200 mL), dry THF (1.1 L) was added to the flask. After cooling to 0°, 2-amino-3-methoxy-2-methyl-1-propanol (61C, 119.16 g, 1.0 mol) was added dropwise to the flask at such a rate that the reaction temperature remained below 30°. The resulting slurry was cooled to 0°. Iodomethane (Aldrich, 141.94 g, 1.0 mol, 62.25 mL) was added dropwise to the mixture at such a rate that the reaction temperature remained below 30°. After the mixture was stirred for 1 h, EtOH (25 mL) was added to quench the reaction. The volume of the reaction was reduced to 200 mL. This material was diluted to 2 L with Et2O, filtered and the solvent removed. Fractional distillation of this material gave 91.02 g (68.3% yield of 1,1-bis-(methoxymethyl)ethylamine, bp 146°-149°, (C,H,N).

1. customTo a 3-necked 3 L RB flask equipped with overhead stirrer, condenser and N2 inlet line
2. washAfter washing with hexane (3×200 mL), dry THF (1.1 L)
3. additionwas added to the flask
4. temperatureAfter cooling to 0°
5. customremained below 30°
6. temperatureThe resulting slurry was cooled to 0°
7. customremained below 30°
8. customto quench
9. customthe reaction
10. filtrationfiltered
11. customthe solvent removed
12. distillationFractional distillation of this material

ORD record

ord-e04fa9e53e2f4a9f98a009dd38d368b1

Source dataset

uspto-grants-1990_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04910218