Chloroacetyl chloride → Acetamide, 2-chloro-N-(m-methoxyphenethyl)-

Temperature

-60 °C

The amine, 2-(3-Methoxy-phenyl)-ethylamine, was taken up as a 0.6 M solution in DCM, followed by addition of TEA (2 equiv.). The mixture was then cooled in an IPA/dry ice bath. When the reaction temperature reached −60° C., a solution of chloroacetylchloride in DCM (2.6 M) was added dropwise so as to keep the temperature below −60° C. After complete addition, the reaction was stirred at −60° C. for 1 h. The reaction was then warmed to −20° C. and filtered over GF filter paper to remove some of the TEA —HCl salt. The filtrate was warmed the rest of the way to rt and transferred to a separatory funnel where it was washed with 1 N HCl (2×) and brine. The organic layer was dried over MgSO4 and concentrated to give a dark purple solid. This crude product was directly used in the next step without further purification.

1. temperatureThe mixture was then cooled in an IPA/dry ice bath
2. customreached −60° C.
3. customthe temperature below −60° C
4. additionAfter complete addition
5. temperatureThe reaction was then warmed to −20° C.
6. filtrationfiltered over GF
7. filtrationfilter paper
8. customto remove some of the TEA —HCl salt
9. temperatureThe filtrate was warmed the rest of the way to rt
10. customtransferred to a separatory funnel
11. washwhere it was washed with 1 N HCl (2×) and brine
12. dry with materialThe organic layer was dried over MgSO4
13. concentrationconcentrated
14. customto give a dark purple solid
15. customThis crude product was directly used in the next step without further purification

ORD record

ord-5aa8a325e536479f97257c448d327cd7

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07491794B2