Benzyl-(6-fluoroindan-1-yl)-amine → 6-Fluoro-2,3-dihydro-1H-inden-1-amine

HRID 2175052Notes

Reaction equation

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]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To 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].

Workup

customPurge the chamber with nitrogen three times
filtrationFilter the mixture through Celite® 521
washwash the solids with methanol
concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record: ord-7651103b0a204b1ab55f99235215a63e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062050B2

Reaction notes

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