Acrylonitrile → HCID 22020947, compound

HRID 900052Notes

Reaction equation

HRID 900052 reaction equation
[NH2:1][C:2]1([CH2:15][OH:16])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[C:17](#[N:20])[CH:18]=[CH2:19]>C(O)C>[OH:16][CH2:15][C:2]1([NH:1][CH2:19][CH2:18][C:17]#[N:20])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 7855Acrylonitrile3×HCID 22020939HCID 22020939, compound

Product 1

HCID 22020947HCID 22020947, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A. mixture of 4-amino-1-(phenylmethyl)-4-piperidinemethanol (0.0182 mol) and 2-propenenitrile (0.0304 mol) in ethanol (80 ml) was stirred and refluxed over the weekend. 2-Propenenitrile (2 ml) was added. The mixture was stirred and refluxed for 5 hours. 2-Propenenitrile (2 ml) was added again. The mixture was stirred and refluxed overnight. The solvent was evaporated. The residue was purified over silica gel on a glass filter (eluent: CH2Cl2/(CH3OH/NH3) 95/5). The desired fractions were collected and the solvent was evaporated, yielding 3-[[4-(hydroxymethyl)-1(phenylmethyl)-4-piperidinyl]amino]-propanenitrile (interm. 10).

Workup

  1. temperaturerefluxed over the weekend
  2. stirringThe mixture was stirred
  3. temperaturerefluxed for 5 hours
  4. stirringThe mixture was stirred
  5. temperaturerefluxed overnight
  6. customThe solvent was evaporated
  7. customThe residue was purified over silica gel on a glass
  8. filtrationfilter (eluent: CH2Cl2/(CH3OH/NH3) 95/5)
  9. customThe desired fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0df80c878d36477e8f99d135cb1f9d44
Source dataset
uspto-grants-2008_04
Patent number
US07358239B2

Reaction notes

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