Acetic Acid → HCID 39235372, compound

To a solution of 4-cyanopiperidine (5.8 g, 53 mmol, J. Org. Chem. 21, 984-986, 1957) in methanol (30 mL) and THF (130 mL) was added with stirring acetone (7.7 mL) and glacial acetic acid (6.0 mL) followed by portionwise addition of sodium cyanoborohydride (6.6 g, 105 mmol). When addition was complete the mixture was stirred overnight at ambient temperature. The solvent was evaporated and to the residue was added 1N hydrochloric (110 mL) until pH 1. The mixture was washed with diethyl ether (100 mL) and the acidic aqueous phase was saturated with potassium carbonate. The alkaline mixture (pH 10) was extracted with ethyl acetate (2×200 mL). The combined organic extracts were dried (MgSO4) and the solvent was evaporated. This afforded 8.2 g of 1-isopropyl-4-cyanopiperidine. 1H NMR 400 MHz, DMSO-d6) δ 0.96 (d, 6H), 1.63-1.73 (m, 2H), 1.80-1.92 (m, 2H), 2.35-2.44 (m, 2H), 2.58-2.67 (m, 2H), 2.69-2.78 (m, 1H), 2.79-2.87 (m, 1H).

1. additionWhen addition
2. customThe solvent was evaporated and to the residue
3. additionwas added 1N hydrochloric (110 mL) until pH 1
4. washThe mixture was washed with diethyl ether (100 mL)
5. extractionThe alkaline mixture (pH 10) was extracted with ethyl acetate (2×200 mL)
6. dry with materialThe combined organic extracts were dried (MgSO4)
7. customthe solvent was evaporated

ORD record

ord-1875b75567c24b6aae33d4b72802a2ef

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07799924B2