Hydrochloric Acid → 147539-53-5

To a stirred mixture of 1-tert-butyloxycarbonylpiperazine (1.10 g, 5.91 mmol), 3-chloro-3-methyl-1-butyne (0.88 ml, 7.81 mmol), THF (10 ml), and NEt3 (1.10 ml, 7.91 mmol) under nitrogen was added copper(I) chloride (45 mg, 0.46 mmol). An exothermic reaction ensued and a precipitate formed. After stirring for 0.5 hours at room temperature water (20 ml) and 1 N aqueous hydrochloric acid (8 ml) were added and the mixture was concentrated under reduced pressure to ⅔ of its original volume. The mixture was washed with ethyl acetate (2×20 ml) and made basic by addition of potassium carbonate (approx. 4 g). Extraction with ethyl acetate (3×20 ml), washing of the combined extracts (30 ml brine), drying with magnesium sulphate, and concentration under reduced pressure yielded 1.15 g (77%) of the title compound as a colourless solid.

1. customAn exothermic reaction
2. customa precipitate formed
3. additionwere added
4. concentrationthe mixture was concentrated under reduced pressure
5. washThe mixture was washed with ethyl acetate (2×20 ml)
6. additionmade basic by addition of potassium carbonate (approx. 4 g)
7. extractionExtraction with ethyl acetate (3×20 ml)
8. washwashing of the combined extracts (30 ml brine)
9. dry with materialdrying with magnesium sulphate, and concentration under reduced pressure

ORD record

ord-06769342517748c18b22a72702beac76

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07208497B2