61381-04-2 → HCID 13276277, compound

HRID 325615Notes

Reaction equation

HRID 325615 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:13][CH2:14][NH2:15])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[CH:16]([O:19][C:20]1[CH:21]=[C:22]([CH2:30][C:31](OCC)=[O:32])[CH:23]=[CH:24][C:25]=1[O:26][CH:27]([CH3:29])[CH3:28])([CH3:18])[CH3:17]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:13][CH2:14][NH:15][C:31](=[O:32])[CH2:30][C:22]2[CH:23]=[CH:24][C:25]([O:26][CH:27]([CH3:28])[CH3:29])=[C:20]([O:19][CH:16]([CH3:18])[CH3:17])[CH:21]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 84069461381-04-2HCID 13276276HCID 13276276, compound

Product 1

HCID 13276277HCID 13276277, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-(3,4-diethoxyphenyl)-ethylamine (40.7 g, 0.195 mole) and ethyl 3,4-diisopropoxyphenylacetate (55.7 g, 0.195 mole) was heated with stirring at 160° C. for 20 hours, allowed to cool and the resulting oil taken up in 700 ml of chloroform. The organic solution was washed 3 times with 100 ml of N hydrochloric acid and then with water to pH 7. The chloroform solution was dried over magnesium sulphate, the solvent removed under reduced pressure and purification effected by chromatography over silica gel. 64.5 g (yield 72%) of product was obtained sufficiently pure to be used in step (b) below.

Workup

  1. temperaturewas heated
  2. temperatureto cool
  3. washThe organic solution was washed 3 times with 100 ml of N hydrochloric acid
  4. dry with materialThe chloroform solution was dried over magnesium sulphate
  5. customthe solvent removed under reduced pressure and purification

Sources & evidence

ORD record
ord-b80ff3cb52f349bdbd4e95cb68c5fcde
Source dataset
uspto-grants-1984_04
Patent number
US04442108

Reaction notes

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