Reaction #2275686

Reaction equation

N-(hydroxyethyl)-amino-2,3-propanediol

HCl

dioxane

2,2-dimethoxypropane

→

liquid

Yield 100.0%

2-[(2,2-Dimethyl-[1,3]-dioxolan-4-yl-methyl)-amino]-ethanol

Yield 100.0%

Solvents

Triethylamine

DMAC

Conditions

Workup

1. 1
   Otherthe solvents removed by rotary evaporation
2. 2
   workup.DISSOLUTIONThe viscous crude mixture was dissolved into triethylamine (30 mL) and ethyl acetate (500 mL)
3. 3
   workup.STIRRINGstirred at RT for 30 min
4. 4
   FiltrationThe mixture was filtered
5. 5
   Washthe collected solid washed several times with ethyl acetate
6. 6
   OtherThe filtrate was then evaporated on a high vacuum rotary evaporator at 40° C.

Procedure

The N-(hydroxyethyl)-amino-2,3-propanediol (16.5 g, 122 mmol) was treated with a solution of HCl in dioxane (33.5 ml, 134 mmol). To this solution were added 2,2-dimethoxypropane (15.3 g, 147 mmol), DMAC (50 mL), and a catalytic amount of para-toluene sulphonic acid (0.006 mol, 1.16 g). The mixture stirred at room temperature for 24 hours. Triethylamine (1 mL) was then added, and the solvents removed by rotary evaporation. The viscous crude mixture was dissolved into triethylamine (30 mL) and ethyl acetate (500 mL) and stirred at RT for 30 min. The mixture was filtered and the collected solid washed several times with ethyl acetate. The filtrate was then evaporated on a high vacuum rotary evaporator at 40° C. to give a yellow liquid (0.122 mol, 99% yield).

Source