Ethyl Acetate → HCID 57949605, compound

HRID 2427593Notes

Reaction equation

CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10]Br.[F:13][C:14]([F:26])([F:25])[C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][CH2:23][NH2:24])[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[F:13][C:14]([F:25])([F:26])[C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][CH2:23][N:24]2[CH2:10][C:5]3[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:3]2=[O:12])[CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromomethyl-benzoic acid methyl ester (1.13 g, 4.9 mmol), 3-(3-trifluoromethyl-phenyl)-propylamine (1 g, 4.9 mmol), and K2CO3 (1.13 g, 8.17 mmol) in toluene (10 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-[3-(3-trifluoromethyl-phenyl)-propyl]-2,3-dihydro-isoindol-1-one (0.658 g, 49%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.02 (m, 2H), 2.76 (t, 2H), 3.69 (t, 2H), 4.36 (s, 2H), 7.36-7.56 (m, 7H), 7.84 (d, 1H). GC-MS: m/z 319 (M)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-f344ffaf1b694fd7b60dda69df77f0e0
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

Loading…