Aluminium lithium hydride → N,N-dimethyl-1-[(2S)-1-(phenylmethyl)-2-piperidinyl]methanamine

HRID 1366701Notes

Reaction equation

[CH3:1][N:2]([CH3:19])[C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][N:2]([CH3:19])[CH2:3][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[CH2:11][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(2S)—N,N-Dimethyl-1-(phenylcarbonyl)-2-piperidinecarboxamide (883 mg, 3.396 mmol) was dissolved in 20 mL of THF, cooled to 0° C., and then LiAlH4 (1.386 mg, 36.54 mmol) was added portion wise. The mixture was heated to 80° C. for 2 h, then allowed to cool to RT. The reaction was quenched in succession with H2O (1.0 mL), 15% aq. NaOH (1.0 mL) and H2O (3.0 mL), and was stirred at room temperature overnight. The contents were filtered, and the filtrate was concentrated in vacuo to provide N,N-dimethyl-1-[(2S)-1-(phenylmethyl)-2-piperidinyl]methanamine (590 mg, 75%). LCMS: (M+H)+: 233.1.

Workup

temperatureThe mixture was heated to 80° C. for 2 h
temperatureto cool to RT
customThe reaction was quenched in succession with H2O (1.0 mL), 15% aq. NaOH (1.0 mL) and H2O (3.0 mL)
filtrationThe contents were filtered
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-6e1e939b25af4622a4cbf57736ce8bab
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

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