Aluminium lithium hydride → 3-(Aminomethyl)-1-benzylpiperidin-4-ol

HRID 396330Notes

Reaction equation

HRID 396330 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([C:15]#[N:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:16][CH2:15][CH:10]1[CH:11]([OH:14])[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 230037331-Benzyl-3-cyano-4-hydroxypiperidine

Product 1

HCID 230037323-(Aminomethyl)-1-benzylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 1-benzyl-3-cyano-4-hydroxypiperidine (2.3 g, 10.64 mmole) and lithium aluminum hydride (0.6 g, 15.97 mmole) in dry tetrahydrofuran (50 ml) was refluxed for 2 hr. The reaction mixture was cooled at 5° C. and quenched with water, aqueous NaOH (10%) and filtered. Filtrate was concentrated to dryness to afford crude 3-aminomethyl-1-benzyl-4-hydroxypiperidine. Yield 2.1 g (89.6%) C13H20N2O, m/z 221 (M+1), PMR (CDCl3): 1.1-1.9 (3H, m, H3 & H5), 2.1 (1H, m, H6), 2.82 (2H, m, H2), 3.4-3.96 (3H, m, H6 & CH2NH2), 4.16 (1H, m, H4), 4.84 (2H, s, N—CH2Ar), 7.34 (5H, m, ArH).

Workup

  1. temperaturewas refluxed for 2 hr
  2. customquenched with water, aqueous NaOH (10%)
  3. filtrationfiltered
  4. concentrationFiltrate was concentrated to dryness

Sources & evidence

ORD record
ord-02438629518c4b32a2d7f60e5d5d2e7e
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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