Ethanol → HCID 20207301, compound

HRID 542203Notes

Reaction equation

HRID 542203 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH2:14][CH:15]3CO3)[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C-]#[N:19].[Na+].[Cl-].[NH4+].[CH2:23]([OH:25])[CH3:24]>>[OH:25][CH:23]([CH:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:9]=1)[CH3:15])[C:24]#[N:19]

Participants

5

Reactant 4

HCID 702EthanolHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 20207303HCID 20207303, compound

Product 1

HCID 20207301HCID 20207301, compound

Procedure

0.74 g (3.2 mmol) of 2-[3-(1-piperidylmethyl)phenyl]methyl-oxirane, 0.294 g (6 mmol) of sodium cyanide and 0.107 g (2 mmol) of ammonium chloride are boiled in 5 ml ethanol/5 ml water for 6 hours. After substantial concentration of the mother liquor by evaporation under vacuum, the residue is taken up in 10 ml of water, and the solution is adjusted to pH 12 with potassium carbonate and extracted with 3×20 ml of methylene chloride. The organic phase yields 0.82 g of a brown oil after dehydration and evaporation under vacuum.

Workup

  1. concentrationAfter substantial concentration of the mother liquor
  2. customby evaporation under vacuum
  3. extractionextracted with 3×20 ml of methylene chloride

Sources & evidence

ORD record
ord-de94d637180d4ac9b43b8d93eaeb6bfc
Source dataset
uspto-grants-1987_04
Patent number
US04656180

Reaction notes

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