Aniline → HCID 19811474, compound

Temperature

100 °C

A mixture of 2-(bromomethyl)tetrahydro-2H-pyran (100 g, 0.558 mol) and aniline (155.96 g, 1.67 mol) was heated at 100° C. under nitrogen overnight and cooled to room temperature. A 3N hydrochloric acid solution (400 mL) was added and the aqueous layer was washed three times with isopropyl ether. The aqueous layer was made basic with 50% sodium hydroxide solution, and the product was extracted three times into isopropyl ether. The combined organic extracts were washed once with water and evaporated under reduced pressure. The resulting oil was poured into water (1400 mL) and stirred. The water was decanted and water (1500 mL) was again added. The aqueous layer was again decanted and the oil was triturated again in water (1500 mL) to give a solid, which was recrystallized from methanol/water and dried under high vacuum to give 78.5 g of product containing one mole of water (67% yield). A 2.0 g portion was recrystallized from methanol/water and dried under high vacuum to give 0.71 g, mp 55°-58° C.

1. temperaturecooled to room temperature
2. washthe aqueous layer was washed three times with isopropyl ether
3. extractionthe product was extracted three times into isopropyl ether
4. washThe combined organic extracts were washed once with water
5. customevaporated under reduced pressure
6. additionThe resulting oil was poured into water (1400 mL)
7. customThe water was decanted
8. additionwater (1500 mL) was again added
9. customThe aqueous layer was again decanted
10. customthe oil was triturated again in water (1500 mL)
11. customto give a solid, which
12. customwas recrystallized from methanol/water
13. customdried under high vacuum

ORD record

ord-ebbfc29dc1a344948d80e2157472f008

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05162322