Hydroxyacetonitrile → HCID 57447694, compound

HRID 1669201Notes

Reaction equation

HRID 1669201 reaction equation
[CH3:1][CH2:2][N:3](CC)CC.Cl.[CH3:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]1.C(#N)CO>O>[CH3:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([CH2:1][C:2]#[N:3])[CH2:12]1

Participants

5

Reactant 3

HCID 7857HydroxyacetonitrileHCID 8471TriethylamineHCID 231420003-Methoxypiperidine--hydrogen chloride (1/1)

Product 1

HCID 57447694HCID 57447694, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Et3N (7.0 mL, 50 mmol) was added to a suspension of 3-methoxypiperidine hydrochloride (281) (McManus, J. M. et al., J. Med. Chem. 1965, 8, 766-776) (3.80 g, 25.0 mmol) and aqueous glycolonitrile (55%, 2.7 mL, 27.6 mmol), and the resulting solution stirred at 70° C. for 1.5 h. The solution was cooled to 20° C. and diluted with water (40 mL). The aqueous layer was extracted with Et2O (4×50 mL), the combined organic fraction dried and the solvent evaporated to give nitrile 282 (3.76 g, 97%) as a colourless oil, which was used without further purification: 1H NMR δ 3.54 (s, 2H, CH2CN), 3.36-3.40 (m, 1H, H-3), 3.37 (s, 3H, OCH3), 2.77 (dd, J=10.9, 3.2 Hz, 1H, H-2), 2.44-2.56 (m, 3H, H-2, H-6), 1.75-1.85 (m, 2H, H-4, H-5), 1.52-1.57 (m, 2H, H-4, H-5).

Workup

  1. temperatureThe solution was cooled to 20° C.
  2. extractionThe aqueous layer was extracted with Et2O (4×50 mL)
  3. customthe combined organic fraction dried
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-ce0877e131c341d08cb1794ca679b32a
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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