Water → N,N-dibenzyl-N-(piperidin-4-ylmethyl)amine

HRID 1743817Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:15]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[CH2:23]([N:14]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:15][CH:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of lithium aluminum hydride (min. 80%, 1.50 g, 40.0 mmol) in tetrahydrofuran (50 ml) was added dropwise a solution of N,N-dibenzylpiperidine-4-carboxamide (EXAMPLE 4, Step 2, 3.08 g, 10.0 mmol) in tetrahydrofuran (50 ml) at 0° C. over 15 min. The mixture was stirred at 0° C. for 30 min and at 40° C. for 4 h. After cooling to 0° C., water (3.3 ml), 15% NaOH aqueous solution (3.3 ml), and then water (10 ml) were carefully added dropwise. The resulting mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo to give 2.85 g (97%) of the title compound as a pale yellow oil.

Workup

temperatureAfter cooling to 0° C.
filtrationThe resulting mixture was filtered through a pad of Celite
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-da2a5baa6f664b0eab9169bd6d0beb33
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07012080B2

Reaction notes

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