Morpholine → 4-[(4-Bromothien-2-YL)methyl]morpholine

To a solution of 4-bromothiophene-2-carbaldehyde 63 (Avocado, UK) (1.20 g, 6.3 mmol) in THF (50 mL) at rt was added dropwise morpholine (0.96 g, 11 mmol). After the reaction was stirred at rt for 5 minutes, NaBH(OAc)3 (3.18 g, 15 mmol) was added in one portion. The resulting mixture was stirred at rt for 3 h. Ethyl acetate (80 mL) was added and then washed with NaHCO3 (20 mL×2) and brine (20 mL). The organic layer was dried with MgSO4. After the solvent was evaporated, the residue was purified by silica gel column chromatography to give 64 (1.31 g). 1H NMR (400 MHz, CDCl3) 6, 2.50–2.52(m, 4H), 2.67 (s, 2H), 3.72–3.75 (m, 4H), 6.87(s, 1H), 7.15 (d, J=1.4 Hz, 1H). MS (EI) m/z (M+H+) 263.

1. stirringThe resulting mixture was stirred at rt for 3 h
2. washwashed with NaHCO3 (20 mL×2) and brine (20 mL)
3. dry with materialThe organic layer was dried with MgSO4
4. customAfter the solvent was evaporated
5. customthe residue was purified by silica gel column chromatography

ORD record

ord-135096dec091405dabee1a3521c3a331

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199119B2