Propylamine → HCID 4716567, compound

To 4-bromobenzaldehyde (100 g, 0.54 mol) and n-propylamine (36.3 g, 0.60 mol) in methanol (100 mL) was added 5% platinum on carbon (1.00 g). This mixture was shaken in a Parr hydrogenation reactor overnight to complete formation of the Schiff base. The reaction was then hydrogenated under 4 atmospheres of hydrogen until the theoretical uptake of hydrogen had been consumed. The catalyst was removed by filtration through a 0.45μ nylon frit and washed with methanol. The filtrate was concentrated under reduced pressure and the residue obtained dissolved in ether (500 mL). The ether solution was washed with water (2×100 mL), 10% sodium bicarbonate solution (2×100 mL), and water (2×100 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford the crude title compound (121.34 g). GC-MS showed this material to be 98.5% pure product containing 1.5% of the desbromo compound; the yield is 96.93% based on the GC purity of the product obtained. A sample of material thus obtained was purified by bulb-to-bulb distillation (bath temperature 130°-150° C., 0.18 torr). 1H NMR (CDCl3, 300 MHz) δ0.92 (t, J=7.4 Hz, 3H), 1.36 (bs, 1H), 1.53 (tq, J1 =J2 =7.4 Hz, 2H), 2.57 (t, J=7.4 Hz, 2H), 3.74 (s, 2H), 7.20 (d, J=9 Hz, 2H), 7.44 (d, J=9 Hz, 2H). IR (film) 1430, 1060 cm-1. MS (DCl/NH3) m/e 228, 230 (M+H)+. Anal calcd for C10H14BrN: C, 52.64; H, 6.18; N, 6.14. Found: C, 53.12; H, 6.24; N, 6.18.

1. customhad been consumed
2. customThe catalyst was removed by filtration through a 0.45μ nylon frit
3. washwashed with methanol
4. concentrationThe filtrate was concentrated under reduced pressure
5. customthe residue obtained
6. washThe ether solution was washed with water (2×100 mL), 10% sodium bicarbonate solution (2×100 mL), and water (2×100 mL)
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-8c845f4352f14b6482da37a40245560d

Source dataset

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05284954