3-Phenylprop-2-enoyl chloride → 2'-[2-(1-Methyl-2-piperidyl)ethyl]-cinnamanilide

HRID 1974097Notes

Reaction equation

HRID 1974097 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:12][C:13]1[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=1[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][N:18]1[CH3:23]>N1C=CC=CC=1>[CH3:23][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[CH2:16][CH2:15][C:14]1[CH:24]=[CH:25][CH:26]=[CH:27][C:13]=1[NH:12][C:1](=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 660233-Phenylprop-2-enoyl chlorideHCID 110852822-(2-Aminophenethyl)-1-methylpiperidine

Product 1

HCID 209816792'-[2-(1-Methyl-2-piperidyl)ethyl]-cinnamanilideYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cinnamoyl chloride (6.0 g., 0.036 mole) is added to a solution of 2-(o-aminophenethyl)-1-methylpiperidine (7.8 g., 0.036 mole) in 100 ml. of pyridine in one portion with vigorous stirring. Stirring is continued for 3 hours and the pyridine solution is then concentrated in vacuo. The resulting residue is taken up in 150 ml. of water and made basic with 40% sodium hydroxide. The basified solution is extracted with several 200 ml. portions of ether, which are combined, washed with water, dried over magnesium sulfate and the ether solvent evaporated. The residue thus obtained crystallizes and is further purified by crystallizing from isopropyl ether providing 8.7 g. (70% yield) of analytically pure 2'-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide melting at 101.5° -103.5° C. (corr.).

Workup

  1. concentrationthe pyridine solution is then concentrated in vacuo
  2. extractionThe basified solution is extracted with several 200 ml
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe ether solvent evaporated
  6. customThe residue thus obtained
  7. customcrystallizes
  8. customis further purified
  9. customby crystallizing from isopropyl ether providing 8.7 g

Sources & evidence

ORD record
ord-0e1bb056fa8a49ca8548c95a88f034d2
Source dataset
uspto-grants-1976_12
Patent number
US04000143

Reaction notes

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