Methylamine → 4-(methylaminomethyl)benzonitrile

4-Cyanobenzaldehyde (12.0 g, 92.0 mmol), methylamine (69 ml of a 2.0M solution in tetrahydrofuran, 137 mmol) and magnesium sulphate (45 g) were stirred in dichloromethane (300 ml) at room temperature for 5 days. The mixture was filtered and the filtrate was concentrated under reduced pressure to leave a yellow oil. The oil was dissolved in methanol (200 ml) and sodium borohydride (4.10 g, 109 mmol) was added cautiously with vigorous stirring. Once the addition was complete the reaction was stirred for 1 hour and the mixture was concentrated under reduced pressure. The residue was dissolved in 1M aqueous sodium hydroxide solution (200 ml) and the mixture was stirred at room temperature for 1 hour. The resulting solution was extracted with dichloromethane (2×200 ml) and the combined organic phases were dried over magnesium sulphate, filtered and concentrated under reduced pressure to provide the title compound (13.4 g) as a pale yellow oil.

1. filtrationThe mixture was filtered
2. concentrationthe filtrate was concentrated under reduced pressure
3. customto leave a yellow oil
4. additionOnce the addition
5. concentrationthe mixture was concentrated under reduced pressure
6. dissolutionThe residue was dissolved in 1M aqueous sodium hydroxide solution (200 ml)
7. stirringthe mixture was stirred at room temperature for 1 hour
8. extractionThe resulting solution was extracted with dichloromethane (2×200 ml)
9. dry with materialthe combined organic phases were dried over magnesium sulphate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure

ORD record

ord-35d661b0ed9e4aceb02a58199a49d960

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07435728B2