HCID 10796970, compound → [1-(2-aminoethyl)piperidin-2-yl]methanol

HRID 226249Notes

Reaction equation

HRID 226249 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[CH2:9][C:10]#[N:11].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:11][CH2:10][CH2:9][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH:3]1[CH2:2][OH:1]

Participants

4

Reactant 2

HCID 10796970HCID 10796970, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 4712031[1-(2-aminoethyl)piperidin-2-yl]methanolYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method follows that of S6 using 2-hydroxymethyl-piperidin-1-yl-acetonitrile (31.96 g, 0.208 mol), LiAlH4 (23.68 g, 0.624 mol) and dry THF (200 mL). The title compound (8.74 g, 27%) was afforded as straw-coloured oil by kugelrohr distillation (225° C., 0.13 mbar). δH (250 MHz; CDCl3); 1.2-1.75 (m, 6H, CH2CH2CH2, CH2CH2CH and CH2CH2CH), 2.2 (m, 1H, 1×NCH2CH2) 2.35 (m, 2H, H2NCH2CH2N), 2.58 (s (broad), 3H, OH and NH2), 2.75 (t, 2H, H2NCH2CH2N), 2.85 (3×d, 1H, 1×NCH2CH2), 2.92 (m, 1H, NCHCH2), 3.4 (2×d, 1H, J=4 Hz and 12 Hz, 1×CHCH2OH) and 3.76 (2×d, 1H, J=4 Hz and 12 Hz, 1×CHCH2OH; FAB MS, m/z(M+H)+ 159.

Sources & evidence

ORD record
ord-f673e5e4948046a4bb7e79cf6d630a8f
Source dataset
uspto-grants-2009_07
Patent number
US07557215B2

Reaction notes

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