Hydrochloric Acid → N,4,4-trimethylcyclohexan-1-amine

To a solution of 4,4-dimethylcyclohexanone (25.2 g) in dry methanol under an atmosphere of nitrogen was added methylamine hydrochloride (13.2 g) and 3 Åmol sieves (1 g). The reaction mixture was stirred for 1 hr then sodium cyanoborohydride (12.7 g) added portionwise. The mixture was stirred for 17 hrs. A saturated solution of hydrogen chloride in methanol (200 ml) was added and the reaction mixture stirred for 1 hr the filtered through hyflo and concentrated in vacuo. The residue was partitioned between 1N sodium hydroxide (300 ml) and dichloromethane (200 ml). The layers were separated and the aqueous re-extracted with dichloromethane (2×200 ml). The combined organics were washed with saturated sodium hydrogen concentrated in vacuo. The residue was distilled under reduced pressure. Bpt 40°-45° C. at 0.1 mmHg. 1H NMR (CDCl s) δ0.92 (6H, s), 1.10-1.30 (5H, m), 1.30-1.50 (2H, m), 1.66-1.72 (2H, m), 2.26 (1H, m), 2.42 (3H, s).

1. stirringThe mixture was stirred for 17 hrs
2. stirringthe reaction mixture stirred for 1 hr the
3. filtrationfiltered through hyflo
4. concentrationconcentrated in vacuo
5. customThe residue was partitioned between 1N sodium hydroxide (300 ml) and dichloromethane (200 ml)
6. customThe layers were separated
7. extractionthe aqueous re-extracted with dichloromethane (2×200 ml)
8. washThe combined organics were washed with saturated sodium hydrogen
9. concentrationconcentrated in vacuo
10. distillationThe residue was distilled under reduced pressure
11. customBpt 40°-45° C.

ORDレコード

ord-7dfc8ddd38c046b0a0691456b7abfb4e

出典データセット

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05618812