(R)-1-(4-Chloro-2-fluoro-phenyl)-propylamine hydrochloride synthesis

3synthesis methods

Product Name:(R)-1-(4-Chloro-2-fluoro-phenyl)-propylamine hydrochloride
CAS Number:856563-04-7
Molecular formula:C9H12Cl2FN
Molecular Weight:224.1

2-Propanesulfinamide, N-[(1R)-1-(4-chloro-2-fluorophenyl)propyl]-2-methyl-, [S(R)]-

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(R)-1-(4-Chloro-2-fluoro-phenyl)-propylamine hydrochloride

856563-04-7
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Yield:856563-04-7 99%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane;ethyl acetate at 20; for 0.5 h;Inert atmosphere;

Steps:

2 Intermediate 2 Step 2

Step 2 To a solution of (R)-(+)-2-methyl-propane-2-sulfinic acid [(R)-1-(4-chloro-2-fluoro- phenyl)-propyl]-amide (19.9 g, 68.2 mmol, 1.0 eq) in EtOAc (500 ml) was added 2.1 M HCI in dioxane (69 ml, 137.1 mmol, 2.0 eq) slowly. The reaction was stirred at room temperature under N₂ for 30 min. The solvents were removed in vacuo and the crude material slurried in 3:1 heptane: Et₂0 (200 ml) for 20 min then filtered and the cake washed with heptanes (2 x 50 ml). The cake was dried in an oven at 35 °C under vacuum for 30 min to give (R)-1-(4-chloro-2- fluoro-phenyl)-propylamine hydrochloride (19.6 g, ¹H NMR >95% excluding solvents, 77% active, 67.7 mmol, 99% yield). 1H NMR (270 MHz, DMSO-d₆): 8.81 (3H, s), 7.77 (1 H, t), 7.52 (1H, dd), 7.41 (1H, dd), 4.33 (1H, q), 2.08-1.76 (2H, m), 0.76 (3H, t).

References:

WO2013/64543,2013,A1 Location in patent:Page/Page column 106-107

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References

2-Propanesulfinamide, N-[(4-chloro-2-fluorophenyl)methylene]-2-methyl-, [N(E),S(R)]-

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References