Methylamine → HCID 19756475, compound

A solution of 5-(2-bromoethyl)-2,3-dihydrobenzofuran (1.5 g-see Preparation 20) in 33% methylamine in methanol (40 ml) was heated at 100° C. in a stainless steel pressure vessel for 6 hours then concentrated in vacuo. The residue was partitioned between dichloromethane (50 ml) and 10% aqueous sodium carbonate (50 ml). The layers were separated and the aqueous layer was further extracted with dichloromethane (2×50 ml). The aqueous layer was concentrated in vacuo to give a solid which was triturated with boiling 2-propanol. The mixture was filtered and the filtrate concentrated in vacuo to give a solid which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 1%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless solid, yield, 0.31 g, m.p. 153°-155° C.

1. concentrationthen concentrated in vacuo
2. customThe residue was partitioned between dichloromethane (50 ml) and 10% aqueous sodium carbonate (50 ml)
3. customThe layers were separated
4. extractionthe aqueous layer was further extracted with dichloromethane (2×50 ml)
5. concentrationThe aqueous layer was concentrated in vacuo
6. customto give a solid which
7. customwas triturated with boiling 2-propanol
8. filtrationThe mixture was filtered
9. concentrationthe filtrate concentrated in vacuo
10. customto give a solid which
11. customwas purified by column chromatography on silica eluting with dichloromethane
12. additioncontaining methanol (0% up to 1%)
13. concentrationconcentrated in vacuo

ORD record

ord-a39c5d29fb8342879d622b334d6f37d8

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05219871