Hydroxyacetonitrile → HCID 18180012, compound
Reaction equation
Cl.[F:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[C:9](#[N:12])[CH2:10]O.C(=O)([O-])[O-].[Na+].[Na+]>O>[F:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:10][C:9]#[N:12])[CH2:5][CH2:4]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
4-Fluoropiperidine HCl (801 mg, 5.74 mmol) was added dropwise to a stirred aqueous solution of glycolonitrile (647 uL of a 52% aqueous solution, 6.31 mmol) at 5° C. Sodium carbonate (912 mg, 8.60 mmol) was added and the solution was stirred at 70° C. for 1.5 h. The solution was cooled, diluted with water (2 mL), washed with Et2O (3×4 ml). The organic fraction was dried and the solvent evaporated to give 2-(4-fluoropiperidin-1-yl)acetonitrile as a colourless oil. The oil was then dissolved in a 7 N solution of ammonia in MeOH (25 mL) and submitted to hydrogenation on the H-Cube using 75 bar of hydrogen pressure at 55 C with a flow rate of 0.8 mL/min and using a Raney nickel catalyst cartridge. After the reaction was complete the solvent was stripped in vacuo to give 2-(4-fluoropiperidin-1-yl)ethanamine as a translucent oil.
Workup
- temperatureThe solution was cooled
- washwashed with Et2O (3×4 ml)
- customThe organic fraction was dried
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-90025fcd8b284a2da4e75c0e55740aaf
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394257B2
Reaction notes
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