2-(3-Hydroxypiperidin-1-YL)acetonitrile → 1-(2-Aminoethyl)piperidin-3-ol
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]#[N:16])[CH2:9]1>C1COCC1>[NH2:16][CH2:15][CH2:14][N:10]1[CH2:11][CH2:12][CH2:13][CH:8]([OH:7])[CH2:9]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
LiAlH4 (2.44 g, 64.2 mmol) was added to dry THF (20 mL) at 0° C. in a three-neck round bottom flask under N2. The solution was stirred for 15 min. before the 3-hydroxypiperidin-1-yl-acetonitrile (3 g, 21.4 mmol), diluted in dry THF (5 mL), was added slowly via syringe. The reaction mixture was then refluxed 5 h before allowing the solution to cool to RT. Excess of LiAlH4 was destroyed by dropwise addition of 2.4 mL of H2O, 2.4 mL of NaOH (15%) and finally EtOAc was added dropwise until no effervesence was observed. The formed granular precipitate (lithium hydroxide and aluminium hydroxide) was filtered off and washed several times with CH2Cl2 and EtOAc. The organic layer was dried (MgSO4) and the solvent was removed in vacuo to yield a thick yellowish oil. The title-compound was purified by kugelrohr distillation (172° C., 0.05 mbar) and obtained as a straw coloured oil (1.95 g, 63%). δH (250 MHz;