Sodium Cyanide → 4-(3-Cyanopropyl)-1-piperidinecarboxaldehyde

HRID 364709Notes

Reaction equation

HRID 364709 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

HCID 8929Sodium CyanideHCID 202397684-(3-Bromopropyl)-1-piperidinecarboxaldehyde

Product 1

HCID 202397594-(3-Cyanopropyl)-1-piperidinecarboxaldehydeYield 61.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. customSolvent was removed
  2. additionadded water (300-400 ml)
  3. extractionextracted with CH2Cl2 (4×200 ml)
  4. dry with materialThe extracts, dried over Na2SO4
  5. customwas purified on silica gel columns
  6. 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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