Triethylamine → 1-(3-Methoxy-4-nitrophenyl)-N,N-dimethylmethanamine

Temperature

0 °C

Triethylamine (5 mL) was added to a solution of 3-methoxy-4-nitrobenzyl alcohol (2.5 g, 13.6 mmol) in 50 mL of methylene chloride, and the mixture was cooled to 0° C. under nitrogen. Methanesulfonyl chloride (1.9 g, 16.3 mmol) was added dropwise and the mixture stirred at this temperature for 1 hour. Triethylamine (5 mL) was added, followed by dimethylamine hydrochloride (1.6 g, 20.4 mmol). After 5 minutes, the cooling bath was removed, and the mixture stirred at ambient temperature for 2.5 hours. The mixture was diluted with methylene chloride (75 mL) and washed with water (3×75 mL), and extracted into dilute aqueous HCl (3×75 mL). The combined aqueous extracts were washed with methylene chloride (3×75 mL), basified (3N NaOH), and extracted into methylene chloride (3×75 mL). The combined organic extracts were washed with water (3×75 mL), dried (MgSO4), and evaporated, providing 1.8 g of the product, in 65% yield: 1H NMR (CDCl3) δ 2.26 (s, 6H), 3.45 (s, 2H), 3.97 (s, 3H), 6.95 (d, J=8.2 Hz, 1H), 7.12 (s, 1H), 7.82 (d, J=8.2 Hz, 1H).

1. waitAfter 5 minutes
2. customthe cooling bath was removed
3. stirringthe mixture stirred at ambient temperature for 2.5 hours
4. additionThe mixture was diluted with methylene chloride (75 mL)
5. washwashed with water (3×75 mL)
6. extractionextracted into dilute aqueous HCl (3×75 mL)
7. washThe combined aqueous extracts were washed with methylene chloride (3×75 mL)
8. extractionextracted into methylene chloride (3×75 mL)
9. washThe combined organic extracts were washed with water (3×75 mL)
10. dry with materialdried (MgSO4)
11. customevaporated

ORD record

ord-957a8b7d19954da7b02af65053a8348a

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481568B2