Bromoacetonitrile → 3-(Hydroxymethyl)-1-piperidineacetonitrile

HRID 226241Notes

Reaction equation

HRID 226241 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.Br[CH2:10][C:11]#[N:12]>C1COCC1>[OH:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][N:1]([CH2:10][C:11]#[N:12])[CH2:2]1

Participants

4

Reactant 2

HCID 11534BromoacetonitrileHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 114919673-(Hydroxymethyl)-1-piperidineacetonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method follows that of S1 using 3-piperidinemethanol (4.79 g, 41.59 mmol), BrCH2CN (1.99 g, 16.64 mmol) and dry THF (25 mL). The title-compound was yielded as a straw-coloured oil (2.35 g, 92%) after flash chromatography using CH2Cl2/CH3OH (9:1) as eluent. dH (250 MHz; CDCl3); 1.05 (m, 1H, CHCH2OH), 1.5-1.9 (m, 5H, OH, CH2CH2CH2 and CH2CH2CH), 2.15 (t, 1H, J=10 Hz, 1×NCH2CH), 2.35 (3×d, 1H, J=4 Hz and J=10 Hz, 1×NCH2CH2), 2.7 (m, 1H, 1×NCH2CH2), 2.85 (2×d, 1H, J=4 Hz and J=12 Hz, 1×NCH2CH), 3.52 (s, 2H, NCH2CN) and 3.45-3.65 (m, 2H, CHCH2OH); dC (62.9 MHz; CDCl3); 24.43, 26.14, 38.55, 46.75, 52.83, 55.73, 65.88 and 114.74 (CN); FAB MS, m/z(M+H)+ 155.

Sources & evidence

ORD record
ord-c828c0572a2b4e03a1139de01a41e796
Source dataset
uspto-grants-2009_07
Patent number
US07557215B2

Reaction notes

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