Reaction #93370

ord-7270018c8e304ab09f9bfd27b2196627

Reaction equation

COc1ccccc1OCCCNCCC(C#N)(c1cc(OC)c(OC)c(OC)c1)C(C)C
alpha-isopropyl-alpha-[2-[N-[3-(2-methoxyphenoxy)propyl]amino]ethyl]-3,4,5-trimethoxyphenylacetonitrile
C=O
formalin
O=CO
formic acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
COc1ccccc1OCCCN(C)CCC(C#N)(c1cc(OC)c(OC)c(OC)c1)C(C)C
desired compound
COc1ccccc1OCCCN(C)CCC(C#N)(c1cc(OC)c(OC)c(OC)c1)C(C)C
Alpha-isopropyl-alpha-[2-[N-[3-(2-methoxyphenoxy)propyl]-N-methylamino]ethyl]-3,4,5-trimethoxyphenylacetonitrile

Reactants

COc1ccccc1OCCCNCCC(C#N)(c1cc(OC)c(OC)c(OC)c1)C(C)C
alpha-isopropyl-alpha-[2-[N-[3-(2-methoxyphenoxy)propyl]amino]ethyl]-3,4,5-trimethoxyphenylacetonitrile
C=O
formalin
O=CO
formic acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas refluxed for 1 hour
  2. 2
    TemperatureAfter cooling, to the mixture
  3. 3
    ExtractionThe solution was extracted with chloroform
  4. 4
    WashThe extract was washed with water
  5. 5
    Otherdried
  6. 6
    Otherevaporated

Procedure

A mixture of 0.39 g of alpha-isopropyl-alpha-[2-[N-[3-(2-methoxyphenoxy)propyl]amino]ethyl]-3,4,5-trimethoxyphenylacetonitrile, 1 ml of 37% formalin, and 1 ml of 90% formic acid was refluxed for 1 hour. After cooling, to the mixture were added water and potassium carbonate to make it alkaline. The solution was extracted with chloroform. The extract was washed with water, dried, and evaporated to give 0.23 g of desired compound as a yellow oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04612329uspto-grants-1986_09