Tetrahydrofuran → 4-Piperidinamine,N-methyl-1-(1-methylethyl)-(9CI)
Reaction equation
Cl.CN.C1COCC1.[CH:9]([N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1)([CH3:11])[CH3:10].[C:19]([BH3-])#[N:20].[Na+]>C(O)(=O)C.C(O)C>[CH:9]([N:12]1[CH2:17][CH2:16][CH:15]([NH:20][CH3:19])[CH2:14][CH2:13]1)([CH3:11])[CH3:10]Participants
7
Conditions
- Temperature
- 60 °C
Procedure
To a stirred mixture of methylamine hydrochloride (2.62 g, 38.8 mmol), THF (30 ml), ethanol (15 ml), N-isopropyl-4-piperidinone (3.0 ml, 20.2 mmol), and acetic acid (3.60 ml) was added sodium cyanoborohydride (30 ml, 1 molar solution in THF, 30 mmol), and the mixture was stirred at 60° C. for 6 hours and then at room temperature overnight. The mixture was concentrated under reduced pressure, water (50 ml) and potassium carbonate (47.0 g) were added, and the mixture was extracted with ethyl acetate (6×50 ml). The combined extracts were dried over magnesium sulphate and concentrated, to yield 3.78 g (quant.) of the title compound as an oil, which was used without further purification.
Workup
- customat room temperature
- customovernight
- concentrationThe mixture was concentrated under reduced pressure, water (50 ml) and potassium carbonate (47.0 g)
- additionwere added
- extractionthe mixture was extracted with ethyl acetate (6×50 ml)
- dry with materialThe combined extracts were dried over magnesium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-af0c3523c8bb45da8c600fd68dc14a8f
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767695B2
Reaction notes
Loading…