Sodium Cyanide → 4-(3-Cyanopropyl)-1-piperidinecarboxaldehyde
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH:11]=[O:12])[CH2:7][CH2:6]1.[C-:13]#[N:14].[Na+]>C(O)C>[C:13]([CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH:11]=[O:12])[CH2:7][CH2:6]1)#[N:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-(3-Bromopropyl)-1-piperidinecarboxaldehyde (60 g, 0.256M) and NaCN (25 g) in ethanol (600 ml) was refluxed for 7 hours, Solvent was removed, added water (300-400 ml) and extracted with CH2Cl2 (4×200 ml). The extracts, dried over Na2SO4 was stripped to dryness which was purified on silica gel columns, eluted with ethylacetate-hexane (8:2 parts by volume) to yield 4-(3-cyanopropyl)-1-piperidinecarboxaldehyde (28.4 g, 61% yield).
Workup
- customSolvent was removed
- additionadded water (300-400 ml)
- extractionextracted with CH2Cl2 (4×200 ml)
- dry with materialThe extracts, dried over Na2SO4
- customwas purified on silica gel columns
- washeluted with ethylacetate-hexane (8:2 parts by volume)
Sources & evidence
- ORD record
- ord-1f45f64f0199471fb4d6fa2609bd7e29
- Source dataset
- uspto-grants-1986_08
- Patent number
- US04605744
Reaction notes
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