Triethylamine → HCID 70270103, compound

Dichloromethane (400 mL), 2-methyl-2-imidazoline (56.38 g, 0.637 mol), and triethylamine (283.51 g, 2.802 mol) are placed in a 2000 mL three-necked round bottomed flask equipped with a reflux condenser, internal thermometer, mechanical stirrer, addition funnel, and argon inlet. The solution is brought to reflux and 15 min later a solution of 6-(N,N-Dimethylamino)hexanoyl chloride.hydrochloride (150 g, 0.700 mol), prepared as described in example II, dissolved in dichloromethane (300 mL) is added dropwise over 45 min. The mixture is refluxed for an additional 2 h before being cooled to room temperature. The salts are filtered and washed with methylene chloride. The combined filtrates are washed with 5% NaHCO3 solution (3×300 mL) and water (300 mL). After drying over MgSO4 and filtration, the organic layer is concentrated first by rotary evaporation at 50° C. and then by Kugelrohr distillation at 60°-70° C. (0.2 mm Hg) to give 95.20 g (66%) of an oil which solidifies on standing.

1. customequipped with a reflux condenser
2. additioninternal thermometer, mechanical stirrer, addition funnel, and argon inlet
3. customprepared
4. additionis added dropwise over 45 min
5. temperatureThe mixture is refluxed for an additional 2 h
6. filtrationThe salts are filtered
7. washwashed with methylene chloride
8. washThe combined filtrates are washed with 5% NaHCO3 solution (3×300 mL) and water (300 mL)
9. dry with materialAfter drying over MgSO4 and filtration
10. concentrationthe organic layer is concentrated first by rotary evaporation at 50° C.
11. distillationby Kugelrohr distillation at 60°-70° C. (0.2 mm Hg)

ORD record

ord-a160a818eb184201a3a2f07d2ee0ebf9

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05686015