Methanol → 3-(1-(Dimethylamino)-2-methylpentan-3-yl)phenol

Temperature

31.5 °C

To a stirred solution of [1RS,2RS]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenyl ester (9 g, 0.02 mol) and methanol (27 ml), a solution of sodium hydroxide (4 g, 0.10 mol) and water (18 ml) was added at 20-25° C. and mixture was stirred at 28-35° C. for 20 hours. Reaction mixture was further stirred at 45-50° C. for 6 hours and solvent was distilled off. Resulting residue was dissolved in demineralised water (30 ml) at ambient temperature and washed with isopropyl ether (2×10 ml). Aqueous layer was separated and aqueous hydrochloric acid (7.3 ml, 30%) was added at 20-25° C. reaction mixture was saturated with sodium chloride and extracted with ethyl acetate (2×50 ml). All ethyl acetate extracts were combined, washed with water, dried and solvent was distilled off to give 4.24 g of title compound.

1. customReaction mixture
2. stirringwas further stirred at 45-50° C. for 6 hours
3. distillationsolvent was distilled off
4. dissolutionResulting residue was dissolved in demineralised water (30 ml) at ambient temperature
5. washwashed with isopropyl ether (2×10 ml)
6. customAqueous layer was separated
7. additionaqueous hydrochloric acid (7.3 ml, 30%) was added at 20-25° C.
8. customreaction mixture
9. extractionextracted with ethyl acetate (2×50 ml)
10. washwashed with water
11. customdried
12. distillationsolvent was distilled off

ORD record

ord-80e1cdf534d746f7a36fcc2bdd21d551

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08552219B2