1-Methyl-3-phenylpropylamine → HCID 15572772, compound

HRID 544365Notes

Reaction equation

HRID 544365 reaction equation
[CH3:1][CH:2]([NH2:11])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12]([C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[O:16][CH2:17][CH:18]1[O:20][CH2:19]1)#[N:13]>C(O)C>[C:12]([C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[O:16][CH2:17][CH:18]([OH:20])[CH2:19][NH:11][CH:2]([CH3:1])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)#[N:13]

Participants

4

Reactant 2

HCID 311601-Methyl-3-phenylpropylamineHCID 126196712-(Oxiran-2-ylmethoxy)benzonitrile

Product 1

HCID 15572772HCID 15572772, compoundYield 613.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In this example, 1.5 g of 1-methyl-3-phenylpropylamine and 1.8 g of 1-(2-cyanophenoxy)-2,3-epoxypropane are refluxed for 1.5 hours in 50 ml of99.5% ethanol. After completion of the reaction, the reaction solution is concentrated under reduced pressure. The residue is then charged on a column packed with silica gel and the elution is carried out with methanol. The main fraction of the eluate is concentrated under reduced pressure. Then, the residue is recrystallized from 200 ml of n-hexane to obtain 20 g of 1-(2-cyanophenoxy)-3-(1-methyl-3-phenylpropylamino)-2-propanol as crystals. (Yield: 62%)

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution is concentrated under reduced pressure
  3. additionThe residue is then charged on a column
  4. washthe elution
  5. concentrationThe main fraction of the eluate is concentrated under reduced pressure
  6. customThen, the residue is recrystallized from 200 ml of n-hexane

Sources & evidence

ORD record
ord-7981143449d14842a9c2a0b52c177a09
Source dataset
uspto-grants-1984_05
Patent number
US04450115

Reaction notes

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