Ammonia → 1-(3-Methoxyphenyl)ethanamine

Temperature

90 °C

To a solution of 300 g of 3-methoxyacetophenone of Formula VII in 1000 ml of 10.9% ammonia in methanol, 300 g of Raney nickel in 100 ml of methanol (Raney nickel was prewashed with 2×150 ml of methanol to remove moisture) was charged, followed by heating to about 90° C. The resultant suspension was agitated at about 90° C. under 4 kg/cm2 anhydrous hydrogen gas pressure for about 45 hours. After completion of the reaction, the reaction mass was cooled to about 30° C. and the suspension was filtered through a celite bed, followed by washing the celite with 300 ml of methanol. The filtrate was distilled completely at about 55° C. under vacuum. To the residue, 300 ml of acetone was charged and distilled completely. To the residue, 900 ml of acetone was charged and dry HCl gas was passed at about 0° C. until the pH of the mass was less than 1. The resultant suspension was stirred at about 5° C. for about 3 hours. Solid was separated by filtration and the solid was washed with 100 ml of acetone. The solid obtained was dried at 50° C. for about 5 hours. The above solid is charged in a 4 neck round bottom flask and stirred for about 10 minutes and PH is adjusted to about 11.0 using 65 ml of caustic lye and extracted with 3×200 ml of dichloromethane. The obtained organic layer is distilled completely distilled at about 45° C. to afford 179.6 g of title compound.

1. customAfter completion of the reaction
2. temperaturethe reaction mass was cooled to about 30° C.
3. filtrationthe suspension was filtered through a celite bed
4. washby washing the celite with 300 ml of methanol
5. distillationThe filtrate was distilled completely at about 55° C. under vacuum
6. additionTo the residue, 300 ml of acetone was charged
7. distillationdistilled completely
8. additionTo the residue, 900 ml of acetone was charged
9. customwas passed at about 0° C. until the pH of the mass
10. customSolid was separated by filtration
11. washthe solid was washed with 100 ml of acetone
12. customThe solid obtained
13. customwas dried at 50° C. for about 5 hours
14. additionThe above solid is charged in a 4 neck round bottom flask
15. stirringstirred for about 10 minutes
16. extractionextracted with 3×200 ml of dichloromethane
17. distillationThe obtained organic layer is distilled completely
18. distillationdistilled at about 45° C.

ORD record

ord-a89afdb62df4451f98ffb12030061107

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08013181B2