C([NH:8][CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[CH2:11][CH2:10]1)C1C=CC=CC=1>[Pd].C(O)C>[F:18][C:15]1[CH:16]=[C:17]2[C:12]([CH2:11][CH2:10][CH:9]2[NH2:8])=[CH:13][CH:14]=1To a high-pressure flask, add 10% palladium on carbon (1.44 g) in ethanol (100 mL). Add a solution of benzyl-(6-fluoroindan-1-yl)-amine (14.44 g, 59.84 mmol) in ethanol (200 mL). Purge the chamber with nitrogen three times, and then with hydrogen three times. Stir vigorously under hydrogen (60 psi) at 50° C. for two hours. Filter the mixture through Celite® 521 and wash the solids with methanol. Concentrate the filtrate in vacuo to give the title compound as a light brown liquid (9.14 g, 100%). MS (ES) m/z=152 [M+1].
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