Triethylsilane → HCID 68753644, compound

Temperature

0 °C

8-Chloro-3,4-dihydrospiro[chromene-2,4′-piperidinium]chloride TFA (10 mL) was added to tert-butyl 8-chloro-4-hydroxy-3,4-dihydro-1′H-spiro[chromene-2,4′-piperidine]-1′-carboxylate (905 mg, 2.56 mmol) and an exotherm was observed. Due to the exotherm, the solution was cooled rapidly to 0° C. and it was treated with triethylsilane (1.634 mL, 10.23 mmol). The mixture was heated to 80° C. for 1.5 h. The resulting mixture was concentrated under vacuum. To the residue was added 4 M HCl in dioxane (4 mL) and the solution was concentrated (this was repeated twice). Then, to the residue was added Et2O and the white solid was triturated under ultrasound, filtered and dried to give the title compound. LC-MS: m/z=238.1, 240.1 (MH+). 1H NMR (500 MHz, DMSO-d6): δ 8.82 (br s, 2 H), 7.27 (d, 1 H), 7.11 (d, 1 H), 6.88 (t, 1 H), 3.29-3.22 (m, 2 H), 3.05 (td, 2 H), 2.81 (t, 2 H), 1.95-1.79 (m, 6 H).

1. temperatureThe mixture was heated to 80° C. for 1.5 h
2. concentrationThe resulting mixture was concentrated under vacuum
3. additionTo the residue was added 4 M HCl in dioxane (4 mL)
4. concentrationthe solution was concentrated (
5. additionThen, to the residue was added Et2O
6. customthe white solid was triturated under ultrasound
7. filtrationfiltered
8. customdried

ORD record

ord-60379d81046a485bbb936b93f8abbc1f

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09168248B2