2-(4-hydroxypiperidin-1-yl)acetonitrile → 1-(2-Aminoethyl)piperidin-4-ol

HRID 226248Notes

Reaction equation

HRID 226248 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]#[N:10])[CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:10][CH2:9][CH2:8][N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 111054492-(4-hydroxypiperidin-1-yl)acetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 27564251-(2-Aminoethyl)piperidin-4-olYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method follows that of S6 using 4-hydroxy-piperidin-1-yl-acetonitrile (18.97 g, 0.136 mol), LiAlH4 (15.48 g, 0.408 mol) and dry THF (150 mL). The title compound (8.56 g, 44%) was afforded as a straw-coloured oil after kugelrohr distillation (178° C., 0.05 mbar). δH(250 MHz; CDCl3); 1.55 (m, 2H, 1×CHCH2CH2 and 1×CH2CH2CH), 1.85 (m, 2H, 1×CHCH2CH2 and 1×CH2CH2CH), 2-2.25 (m, 5H, NCH2CH2, NCH2CH2 and OH), 2.38 (t, 2H, H2NCH2CH2N), 2.72 (t, 4H, H2NCH2CH2N, NH2) and 3.65 (m, 1H, CH2CHOH); δC(62.9 MHz; CDCl3); 34.56, 38.98, 51.35, 60.84 and 67.64; FAB MS, m/z(M+H)+ 145; IR υmax/cm−1; 3375 (broad), 1600, 1460, 1370, 1290 and 1070.

Sources & evidence

ORD record
ord-17962dd349794bb29f13763a7cc9c213
Source dataset
uspto-grants-2009_07
Patent number
US07557215B2

Reaction notes

Loading…