Semicarbazide hydrochloride → 4-[3-(1-Piperidinylmethyl)phenoxy]butanal semicarbazone

HRID 485375Notes

Reaction equation

HRID 485375 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[O:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.N[NH:22][C:23]([NH2:25])=[O:24]>C(O)C.[Ni]>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[O:11][CH2:12][CH2:13][CH2:14][CH:15]=[N:16][NH:22][C:23]([NH2:25])=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 11236Semicarbazide hydrochlorideHCID 197625514-{3-[(Piperidin-1-yl)methyl]phenoxy}butanenitrile

Product 1

HCID 540828474-[3-(1-Piperidinylmethyl)phenoxy]butanal semicarbazoneYield 76.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-[3-(1-piperidinylmethyl)phenoxy]butannitrile (51.6 g) sodium acetate (73.8 g) and semicarbazide hydrochloride (77.6 g) in 50% aqueous ethanol (1 L) was hydrogenated over Raney Nickel (50 g). The catalyst was removed by filtration. The filtrate was partially evaporated, made basic with potassium carbonate and extracted with ethyl acetate. The organic extract was evaporated to leave an oil which was purified by column chromatography to give the title compound as a pale yellow oil (48.6 g); tlc System B, Rf 0.8.

Workup

  1. customThe catalyst was removed by filtration
  2. customThe filtrate was partially evaporated
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. customwas evaporated
  6. customto leave an oil which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-177cd244e2084059a963536889e9fe4b
Source dataset
uspto-grants-1985_08
Patent number
US04536508

Reaction notes

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