Methylamine → HCID 10125080, compound

Temperature

0 °C

2-chloro-1-(1-methyl-1H-pyrrol-2-yl)ethanol (Croce, P. D.; Ferraccioli, R.; Ritieni, A. Synthesis, 1990, 212-213) (2.05 g) is dissolved in methanol (40 mL) and added dropwise to a 2.0 M solution of methylamine in methanol (65 mL) at 0° C. The reaction mixture is stirred at 0° C. for 1 h and then allowed to warm to room temperature. The reaction mixture is stirred at room temperature for 18 h and then cooled to 0° C. Sodium borohydride (0.738 g) in H2O (40 mL) is added dropwise. The reaction mixture is stirred at 0° C. for 30 min and then allowed to warm to room temperature. The reaction mixture is stirred at room temperature for 18 h. An additional 0.738 g (19.5 mmol) of sodium borohydride is added and the reaction mixture is stirred at room temperature for 18 h. The reaction is quenched with a 1 N HCl solution and then concentrated in vacuo to remove methanol. The aqueous layer is adjusted to pH 12 with a 2 N NaOH solution and extracted with CH2Cl2 (4×100 mL). The combined organic layers are dried (MgSO4), filtered, and concentrated in vacuo. The resulting yellow oil is crystallized from ethyl acetate to yield 0.772 g of the title compound as a white solid.

1. customSynthesis, 1990, 212-213) (2.05 g)
2. temperatureto warm to room temperature
3. stirringThe reaction mixture is stirred at room temperature for 18 h
4. temperaturecooled to 0° C
5. stirringThe reaction mixture is stirred at 0° C. for 30 min
6. temperatureto warm to room temperature
7. stirringThe reaction mixture is stirred at room temperature for 18 h
8. stirringthe reaction mixture is stirred at room temperature for 18 h
9. customThe reaction is quenched with a 1 N HCl solution
10. concentrationconcentrated in vacuo
11. customto remove methanol
12. extractionextracted with CH2Cl2 (4×100 mL)
13. dry with materialThe combined organic layers are dried (MgSO4)
14. filtrationfiltered
15. concentrationconcentrated in vacuo
16. customThe resulting yellow oil is crystallized from ethyl acetate

ORD record

ord-cdb4723f30e24162bcab419df6d8a413

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06852731B2