Epichlorohydrin → 1-Amino-3-({[4-(aminomethyl)cyclohexyl]methyl}amino)propan-2-ol

Temperatur

5 °C

1,4-Cyclohexanebis(methylamine) (14.2 g., 0.1 mole) is dissolved in 50 ml. of anhydrous methyl alcohol and the solution cooled to +5° C. in an ice bath. Epichlorohydrin (9.3 g., 0.1 mole) is added in a 2-minute period and the temperature maintained at +5° C. for 2 hours; reaction is allowed to continue at 10° C-15° C. until thin layer chromatography of an aliquot (silica gel plate with development using a solution of 1 volume concentrated aqueous ammonium hydroxide in 4 volumes of methyl alcohol) indicated nearly complete conversion of the starting diamine to the propylene chlorohydrin. The solution is then added to 100 ml. of dry with methyl alcohol previously saturated at 0° C. with dry ammonia gas by continuous dropwise flow at +5° C. with good agitation and external cooling. After stirring 2 hours at °5° C., it is allowed to warm to 20° C. and mixed overnight. The reaction is competed by heating at 45° C.-55° C. for 6 hours. The solvent and ammonia was removed by stripping and the product purified using fractional distillation under reduced pressure.

1. temperaturethe temperature maintained at +5° C. for 2 hours
2. customreaction
3. customto continue at 10° C-15° C. until thin layer chromatography of an aliquot
4. additionThe solution is then added to 100 ml
5. dry with materialof dry with methyl alcohol previously saturated at 0° C. with dry ammonia gas by continuous dropwise flow at +5° C. with good agitation and external cooling
6. temperatureto warm to 20° C.
7. additionmixed overnight
8. temperatureby heating at 45° C.-55° C. for 6 hours
9. customThe solvent and ammonia was removed
10. customthe product purified
11. distillationdistillation under reduced pressure

ORD-Eintrag

ord-2323f2d7a0ab4edcb487269133029d6f

Quelldatensatz

uspto-grants-1978_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04070400