Formic Acid → Alpha-isopropyl-alpha-[3-[N-[2-(2-methoxyphenoxy)ethyl]-N-methylamino]propyl]-3,4-dimethoxyphenylacetonitrile

HRID 65091Notes

Reaction equation

HRID 65091 reaction equation
[CH:1]([C:4]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=1)([CH2:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])[C:5]#[N:6])([CH3:3])[CH3:2].C=O.[CH:34](O)=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH:1]([C:4]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=1)([CH2:7][CH2:8][CH2:9][N:10]([CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])[CH3:34])[C:5]#[N:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 13714717HCID 13714717, compound

Product 1

HCID 13714723Alpha-isopropyl-alpha-[3-[N-[2-(2-methoxyphenoxy)ethyl]-N-methylamino]propyl]-3,4-dimethoxyphenylacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2.35 g of alpha-isopropyl-alpha-[3-[N-[2-(2-methoxyphenoxy)ethyl]amino]propyl]-3,4-dimethoxyphenylacetonitrile, 8 ml of 37% formalin, and 16 ml of 90% formic acid was stirred for 1 hour at 110° C. After cooling, to the mixture were added water and potassium carbonate to make it alkaline. The solution was extracted with chloroform and the extract was washed with water, dried, and evaporated. The residue was chromatographed on silica gel using chloroform as an eluent to give 1.30 g of the desired compound as a pale yellow oil.

Workup

  1. temperatureAfter cooling, to the mixture
  2. extractionThe solution was extracted with chloroform
  3. washthe extract was washed with water
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-cc569b6f1a1549a99702b4408dea148b
Source dataset
uspto-grants-1986_09
Patent number
US04612329

Reaction notes

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