Hydrochloric Acid → Methyl-[1-(4-trifluoromethyl-phenyl)-piperidin-4-ylmethyl]-amine

HRID 1047388Notes

Reaction equation

C(O[C:6](=O)[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[CH3:6][NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:19][CH:20]=2)[CH2:11][CH2:10]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of [1-(4-trifluoromethyl-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester (45 g; 126 mmol, prepared in accordance with Example 55) in tetrahydrofuran (450 mL) was added over 7 min to a molar solution of lithium aluminium hydride in tetrahydrofuran (377 mL). The resulting mixture was heated to 100° C., and then maintained at that temperature for 195 min. Afterward, the mixture was allowed to cool to room temperature and then poured onto a mixture of ice (500 g) and of 2 N aqueous HCl (350 mL). The organic solvents were removed by evaporation under reduced pressure, and the aqueous phase was basified to a pH of 11 by adding 2 N aqueous NaOH. This resulting in a precipitate, which was filtered and dried at 40° C. under a pressure of 3 mbar to afford the desired product (17.7 g; 65 mmol).

Workup

temperaturemaintained at that temperature for 195 min
temperatureto cool to room temperature
customThe organic solvents were removed by evaporation under reduced pressure
additionby adding 2 N aqueous NaOH
filtrationThis resulting in a precipitate, which was filtered
customdried at 40° C. under a pressure of 3 mbar

Sources & evidence

ORD record: ord-905152e7a90e4901b8ab76f6eed74304
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569495B2

Reaction notes

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