Reaction #95207

Reaction equation

tetramethylguanidine

4,4'-bis(N,N-dimethylamino)benzhydrol

methyl ether

tetrahydrofuran

→

blue crystals

4-[[Bis(p-dimethylaminophenyl)methoxy]acetyl]Morpholine

Solvents

n-hexane

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   FiltrationThe solution was filtered hot
3. 3
   Temperaturecooled
4. 4
   Otherto precipitate a white solid
5. 5
   OtherThe solid was recrystallized from 350 ml of methyl cyclohexane

Procedure

A solution of 4,4'-bis(N,N-dimethylamino)benzhydrol, methyl ether (9.0 g, 0.032 mole), glycol morpholinamide (4.6 g, 0.032 mole), 150 ml of tetrahydrofuran, 250 ml of n-hexane and 4 drops of methanesulfonic acid was refluxed for about 8 hours, during which time an additional 200 ml of solvent was added. The volume was reduced to 200 ml and the color was discharged with tetramethylguanidine. The solution was filtered hot and then cooled to precipitate a white solid. The solid was recrystallized from 350 ml of methyl cyclohexane to give 4.9 g of blue crystals; mp 147.8°-150° C.

Source