Ethanol → HCID 86739256, compound

HRID 364707Notes

Reaction equation

HRID 364707 reaction equation
BrCC[CH:4]1[CH2:9][CH2:8][N:7]([CH:10]=[O:11])[CH2:6][CH2:5]1.[C-:12]#[N:13].[Na+].[CH2:15](O)[CH3:16]>>[C:12]([CH2:15][CH2:16][CH:6]1[CH2:5][CH2:4][CH2:9][CH2:8][N:7]1[CH:10]=[O:11])#[N:13]

Participants

4

Reactant 3

HCID 702EthanolHCID 8929Sodium CyanideHCID 134731474-(2-Bromoethyl)-1-piperidinecarboxaldehyde

Product 1

HCID 86739256HCID 86739256, compoundYield 50%

Procedure

4-(2-Bromoethyl)-1-piperidinecarboxaldehyde (47 g, 0.213M) and NaCN (24 g) in ethanol (470 ml) was refluxed for 4 hours. Solvent was removed, added water (30 ml) and extracted with methylene chloride (4×200 ml). The extracts, dried over NaSO4, were stripped to dryness and then purified on silica gel columns eluted with ethyl acetate to give 4-(2-cyanoethyl-1-piperidinecarboxaldehyde (16 g, 50% yield).

Workup

  1. customSolvent was removed
  2. additionadded water (30 ml)
  3. extractionextracted with methylene chloride (4×200 ml)
  4. dry with materialThe extracts, dried over NaSO4
  5. custompurified on silica gel columns
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-23ac1bfe7f86476aa97d99bfbb9a2360
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Reaction notes

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