Acrylonitrile → HCID 18694166, compound

HRID 1870988Notes

Reaction equation

HRID 1870988 reaction equation
[C:1]1([CH2:7][NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][C:13]3[CH:16]=[CH:17][C:18]4[CH2:22][CH2:21][CH2:20][C:19]=4[C:12]=3[O:11]2)C=CC=C[CH:2]=1.C(#[N:26])C=C.[H][H]>C(O)C>[O:11]1[C:12]2[C:19]3[CH2:20][CH2:21][CH2:22][C:18]=3[CH:17]=[CH:16][C:13]=2[CH2:14][CH2:15][CH:10]1[CH2:9][NH:8][CH2:7][CH2:1][CH2:2][NH2:26]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 18694202HCID 18694202, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18694166HCID 18694166, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate (14-a) (0.02 mol) and 2-propenenitrile (0.2 mol) in ethanol (100 ml) was stirred and refluxed overnight. The solvent was evaporated. The residue was dissolved in methanol. Palladium on activated carbon (10%) (2 g) was added and the mixture was hydrogenated. After uptake of hydrogen (3 eq.), the catalyst was filtered off and the filtrate was evaporated, yielding 5.2 g of (±)-N-[(2,3,4,7,8,9-hexahydrocyclopenta[h]-1-benzopyran-2-yl)methyl]-1,3-propanediamine (interm. 15-a).

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in methanol
  4. additionPalladium on activated carbon (10%) (2 g) was added
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-e91fba97a75049e088ea116b5bfb686f
Source dataset
uspto-grants-2000_08
Patent number
US06100268

Reaction notes

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