2-Amino-N-(1-benzylpiperidin-4-yl)-3-fluorobenzamide → N-(2-Amino-3-fluorobenzyl)-1-benzylpiperidin-4-amine

HRID 2250276Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:9]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)=O>O1CCOCC1>[NH2:7][C:8]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:9]=1[CH2:10][NH:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a refluxing suspension of lithium aluminum hydride (16.1 g, 424 mmol, 3.50 equiv.) in dioxane (800 mL) was added a solution of 2-amino-N-(1-benzylpiperidin-4-yl)-3-fluorobenzamide (39.7 g, 121 mmol) in dioxane (250 mL) at such a rate that gas evolution was limited to a safe flow. Upon completion of the addition, the resulting suspension was heated at reflux for 4 h. The reaction was cooled to 0° C., and quenched by the cautious addition of 20% potassium hydroxide. Upon formation of a white, filterable precipitate, the solid was filtered through a course glass sintered funnel, and the eluent concentrated to give 36.3 g (96%) as a light yellow oil which was used without purification. Mass spec.: 314.29 (MH)+.

Workup

additionUpon completion of the addition
temperaturethe resulting suspension was heated
temperatureat reflux for 4 h
customquenched by the cautious addition of 20% potassium hydroxide
filtrationUpon formation of a white, filterable precipitate, the solid was filtered through a course glass sintered funnel
concentrationthe eluent concentrated
customto give 36.3 g (96%) as a light yellow oil which
customwas used without purification

Sources & evidence

ORD record: ord-e8ef8fe9de584ee9b2a27afe5e95f2b9
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314883B2

Reaction notes

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