Hydrochloric Acid → 2-Piperidinylidene-ethanenitrile
Reaction equation
COC(=O)[C:4]([C:11]#[N:12])=[C:5]1[CH2:10][CH2:9][CH2:8][CH2:7][NH:6]1.Cl>[OH-].[Na+]>[NH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:5]1=[CH:4][C:11]#[N:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A suspension of cyano-2-piperidinylidene-ethanoic acid methyl ester (1.4 g, 7.76 mmol) in 25 mL 1M NaOH was heated at 100° C. for 30 mins. The reaction mixture was cooled to 0° C. and acidifed to pH 5-6 by adding conc. HCl, then extracted with 3×50 mL acetate. The organic phases were combined, dried, and concentrated. The crude product was purified on flash column to afford 2-piperidinylidene-ethanenitrile (590 mg, 62%).
Workup
- temperatureThe reaction mixture was cooled to 0° C.
- extractionextracted with 3×50 mL acetate
- customdried
- concentrationconcentrated
- customThe crude product was purified on flash column
Sources & evidence
- ORD record
- ord-4c7abc2f4e7d4669a4cf390ed6ebbd90
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198456B2
Reaction notes
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