Triethylamine → HCID 10268651, compound

Temperature

0 °C

The above prepared (2S)-2-(4-bromophenoxy)propylamine was combined in a 500 mL 3-neck round bottomed flask with triethylamine (5.7 mL) and methylene chloride (110 mL), fitted with a thermometer, stirbar, and in a nitrogen system. The reaction mixture was cooled to 0° C. in an ice bath, with stirring, and isopropylsulfonyl chloride (2.75 mL, 24.585 mmol) was added by syringe. The mixture was stirred overnight, gradually becoming room temperature. The reaction was quenched with 100 mL water, and extracted two times with 100 mL methylene chloride. The organic extractions were combined, and washed with 200 mL brine, dried with sodium sulfate, filtered and concentrated in-vacuo, yielding 2.08 g viscous brown oil. This material was further purified using one Waters Prep-Pak® on a Waters Prep 2000 HPLC, in a 3:1 hexanes:ethyl acetate solvent system to provide the final title compound (1.63 g, 30%) as a viscous yellow oil.

1. customfitted with a thermometer, stirbar
2. stirringThe mixture was stirred overnight
3. customgradually becoming room temperature
4. customThe reaction was quenched with 100 mL water
5. extractionextracted two times with 100 mL methylene chloride
6. extractionThe organic extractions
7. washwashed with 200 mL brine
8. dry with materialdried with sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in-vacuo

ORD record

ord-08ab7f8e98c24e6ea9921d7a68e4c708

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06911476B2