Acetone → HCID 19097396, compound

A mixture of 2,3,4-trimethyl-3-piperidinepropanol (13.0 g, 70 mmol), acetone (400 mL), methanol (300 mL), sodium cyanoborohydride (4.4 g, 70 mmol), 3A molecular sieves (30 g) and acetic acid (4.0 mL, 70 mmol) was stirred under a nitrogen atmosphere for 2 hours. The pH was readjusted to a pH of 5 by the addition of 1.5 mL of additional acetic acid and the reaction mixture was stirred for 24 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in water (200 mL) and acetone (20 mL) and was acidified with concentrated hydrochloric acid. The mixture was basified with 10% NAOH and extracted with ether (4×300 mL) . The ether extracts were combined, washed with brine and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by a Kugelrohr distillation at 0.1 mm Hg and 100-110° C. to afford 15.7 g (99%) of 2,3. 4-trimethyl-l- (1-methylethyl)-3-piperidinepropanol as a colorless oil.

1. stirringthe reaction mixture was stirred for 24 hours
2. filtrationThe reaction mixture was filtered
3. concentrationthe filtrate was concentrated in vacuo
4. dissolutionThe residue was dissolved in water (200 mL)
5. extractionextracted with ether (4×300 mL)
6. washwashed with brine
7. dry with materialdried over Na2SO4
8. customThe solvent was removed in vacuo
9. distillationthe residue was purified by a Kugelrohr distillation at 0.1 mm Hg and 100-110° C.

ORD record

ord-dcfa93949724403793cd9c7e296c2c53

Source dataset

uspto-grants-1994_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05290789