Acetic Acid → HCID 68530554, compound

To a solution of 3-(3,5-dichloro-phenyl)-1-[4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-1-methyl-urea (˜0.10 g, 0.17 mmol) in ClCH2CH2Cl (1 mL) was added cyclopropanecarboxaldehyde (0.016 mL, 0.204 mmol, 1.2 eq.). The mixture was stirred at room temperature for 15 min and then HOAc (0.01 mL, 1% v/v) was added. The reaction was stirred for a further 1 h. Na(OAc)3BH (0.054 g, 0.255 mmol, 1.5 eq.) was added and the reaction was stirred at room temperature for 12 h. It was diluted with EtOAc (10 mL) and washed with saturated NaHCO3 (10 mL) and saturated brine (10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated by rotary evaporation to give 1-[1-cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-3-(3,5-dichloro-phenyl)-1-methyl-urea (0.094 g, 95%). Crude 1H NMR (CDCl3): δ 7.83 (d, 2H), 7.22 (m, 4H), 7.05 (s, 1H), 6.01 (br.s, 1H), 3.50 (s, 2H), 2.97 (d, 2H), 2.83 (s, 3H), 2.36 (m, 2H), 2.27 (m, 2H), 2.09 (m, 2H), 0.91 (br.m, 1H), 0.58 (d, 2H), 0.15 (d, 2H).

1. stirringThe reaction was stirred for a further 1 h
2. stirringthe reaction was stirred at room temperature for 12 h
3. washwashed with saturated NaHCO3 (10 mL) and saturated brine (10 mL)
4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated by rotary evaporation

ORD record

ord-01db5e57f6f04d28a2d7cf3780e005f7

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06887889B2