Cyclopentylamine → 1-[3-Chloro-6-(2-cyclopentylamino-ethoxy)-4-methoxy-2-methyl-5-(3-phenyl-propoxy)-phenyl]-ethanone

https://huagongshe.com/reaction/219472

Participants

Role	Name	HCID	Charge
Reactant	Cyclopentylamine	HCID 2906	—
Reactant	1-[2-(2-Bromo-ethoxy)-5-chloro-4-methoxy-6-methyl-3-(3-phenyl-propoxy)-phenyl]-ethanone	HCID 59583495	—
Product	1-[3-Chloro-6-(2-cyclopentylamino-ethoxy)-4-methoxy-2-methyl-5-(3-phenyl-propoxy)-phenyl]-ethanone	HCID 25254524	68%

Reaction Conditions

Temperature	65 °C

Reaction Steps

Example 34b (217 mg, 0.48 mmol) was reacted with cyclopentylamine as described under General Procedure B (except heated to 65° C.) and the crude was purified by flash chromatography (silica-gel, MeOH/DCM 5:95) yielding the title compound (151 mg, 68%) as an oil. 1H NMR (300 MHz, CDCl3) δ 7.32-7.19 (m, 5H), 4.14 (t, J=5.1 Hz, 2H), 4.07 (t, J=6.3 Hz, 2H), 3.88 (s, 3H), 3.24-3.04 (m, 1H), 2.87-2.79 (m, 4H), 2.49 (s, 3H), 2.19 (s, 3H), 2.10-2.04 (m, 2H), 1.85-1.78 (m, 3H), 1.69-1.66 (m, 2H), 1.56-1.51 (m, 2H), 1.35-1.31 (m, 2H). MS (ES+) m/z 460 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08202513B2
Source dataset	uspto-grants-2012_06
ORD ID	ord-03eec98650844c1a8bc801bd4e464493
Source note	uspto-grants-2012_06