Triethylamine → HCID 22660961, compound

Temperature

22 °C

A mixture of 4,4′-difluorobenzophenone (2.18 g, 10.0 mmol) in anhydrous ethanol (15 ml) was treated successively with titanium (IV) isopropoxide (5.9 ml, 20.0 mmol), methylamine hydrochloride (1.35 g, 20.0 mmol) and triethylamine (2.8 ml, 20.0 mmol).The resulting mixture was stirred at 22° C. for 18 h and then treated with sodium borohydride (0.57 g, 15.0 mmol). After 6 h at 22° C., the reaction mixture was quenched by the addition of 2N aqueous ammonia (30 ml) and the resulting precipitate was filtered and washed with dichloromethane. The organic layer was collected and extracted with 1N hydrochloric acid. The aqueous phase was then treated with 2N aqueous sodium hydroxide (pH 11) and extracted twice with dichloromethane. The combined extracts were dried (magnesium sulfate) and concentrated. Distillation of the residue in vacuo gave 2.12 g (91%) of the title amine as a clear oil: bp 85-90° C./0.2 torr, (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (CDCl3) δ (ppm): 2.40 (3H, s, NCH3), 4.68 (1H, s, CH benzhydryl), 7.0 (4H, m, aromatics), 7.35 (4H, m, aromatics). Anal. Calcd for C14H13F2N: C, 72.09; H, 5.62; N, 6.0. Found: C, 71.76; H, 5.76; N, 5.84.

1. customresulting mixture
2. waitAfter 6 h at 22° C.
3. customthe reaction mixture was quenched by the addition of 2N aqueous ammonia (30 ml)
4. filtrationthe resulting precipitate was filtered
5. washwashed with dichloromethane
6. customThe organic layer was collected
7. extractionextracted with 1N hydrochloric acid
8. additionThe aqueous phase was then treated with 2N aqueous sodium hydroxide (pH 11)
9. extractionextracted twice with dichloromethane
10. dry with materialThe combined extracts were dried (magnesium sulfate)
11. concentrationconcentrated
12. distillationDistillation of the residue in vacuo

ORD record

ord-ec9c88124ee049efa8529d7df5a24a74

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06803378B2