Aluminium lithium hydride → HCID 131737118, compound

HRID 60791Notes

Reaction equation

HRID 60791 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([CH3:14])[C@@H:9]2[C:15]([NH2:17])=O)=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([CH3:14])[C@@H:9]2[CH2:15][NH2:17])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 131737119HCID 131737119, compound

Product 1

HCID 131737118HCID 131737118, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

rac-cis-1-(4-Methoxybenzyl)-3-methylpiperidine-2-carboxamide (0.61 g, 2.33 mmol) was added portionwise to a suspension of LiAlH4 (0.30 g, 7.50 mmol) and THF (12 mL) and heated to reflux for 14 h. The reaction mixture was then cooled to 0° C. and quenched with water and NaOH (aq.). The resulting mixture was stirred at rt for 1 h, filtered and the filtrated was concentrated in vacuo to provide rac-cis-(1-(4-methoxybenzyl)-3-methylpiperidin-2-yl)methanamine as a colorless oil, used as-is without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 14 h
  3. customquenched with water and NaOH (aq.)
  4. filtrationfiltered
  5. concentrationthe filtrated was concentrated in vacuo

Sources & evidence

ORD record
ord-b54698c5c3d54d5c80f3cd7390ff5c49
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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