Isopropanol → (R)-N-methyl-3-hydroxy-3-phenylpropylamine hemioxalate salt

A solution of (R)-3-chloro-1-phenylpropanol (1.0 g, 5.85 mmol) and a catalytic amount of sodium iodide in ethanol (7 mL) and 40% methylamine aqueous solution (15 mL) was stirred at 60° C. for 7 hours. The reaction mixture was evaporated to 3 mL, and the pH of the solution was adjusted to pH>12 via the addition of aqueous NaOH solution. The mixture was then extracted with toluene twice and the combined extracts were washed with brine. The toluene layer was evaporated to dryness and the residue dissolved in toluene (5 mL) and isopropanol (5.mL) and oxalic acid dihydrate (0.4 g, 3.2 mmol) was added. It was stirred at room temperature for 2Hours and the suspension was filtered and rinsed with toluene/isopropanol to provide 0.9 g of (R)—N-methyl-3-hydroxy-3-phenylpropylamine hemioxalate salt as an off-white solid. 1H NMR (D2O) δ 7.5-7.2 (m, 5H), 4.8 (at, J=6.6 Hz, 1H), 5.15-2.9 (m, 2H), 2.64 (s, 3H), 2.2-2.0 (m, 2H). Elemental Analysis for C11H16NO3; Calculated: H 7.67%; C 62.84%; N 6.66%.

1. customThe reaction mixture was evaporated to 3 mL
2. additionthe pH of the solution was adjusted to pH>12 via the addition of aqueous NaOH solution
3. extractionThe mixture was then extracted with toluene twice
4. washthe combined extracts were washed with brine
5. customThe toluene layer was evaporated to dryness
6. dissolutionthe residue dissolved in toluene (5 mL)
7. filtrationthe suspension was filtered
8. washrinsed with toluene/isopropanol

ORD record

ord-464db26ddc9c4dae81070de3b4881d17

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07485754B2