Triethylamine → N-(2-Chlorocinnamoyl)-3-propyloxyphenethylamine

HRID 1073240Notes

Reaction equation

HRID 1073240 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][NH2:13])[CH:8]=[CH:9][CH:10]=1)[CH2:2][CH3:3].C(OC1C=C(CCN)C=CC=1)CCC.C(N(CC)CC)C.[Cl:35][C:36]1[CH:46]=[CH:45][CH:44]=[CH:43][C:37]=1[CH:38]=[CH:39][C:40](Cl)=[O:41]>C(#N)C.O>[Cl:35][C:36]1[CH:46]=[CH:45][CH:44]=[CH:43][C:37]=1[CH:38]=[CH:39][C:40]([NH:13][CH2:12][CH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[CH:6]=1)=[O:41]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2737382HCID 2737382, compoundHCID 15205618103686-13-1HCID 22379525HCID 22379525, compound

Product 1

HCID 53771533N-(2-Chlorocinnamoyl)-3-propyloxyphenethylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2-(3-propyloxyphenyl)ethylamine prepared in a manner analogous to that described in Example 1E (2.69 g) in acetonitrile (40 cm3) was added triethylamine (3 cm3). A solution of 2-chlorocinnamoyl chloride (3.6 g) in acetonitrile (20 cm3) was added slowly, the reaction mixture being cooled in an ice bath. When addition was complete, the mixture was stirred at room temperature for 40 minutes, treated with water (60 cm3) and SVM (2 cm3) and stirred well. The resulting precipitate was filtered off, washed and air-dried (5.49 g) m.p. 96°-99° C.

Workup

  1. temperaturethe reaction mixture being cooled in an ice bath
  2. additionWhen addition
  3. stirringstirred well
  4. filtrationThe resulting precipitate was filtered off
  5. washwashed
  6. customair-dried (5.49 g) m.p. 96°-99° C.

Sources & evidence

ORD record
ord-e9e8ff2f67384f5b904db53b516dd7c5
Source dataset
uspto-grants-1990_11
Patent number
US04968698

Reaction notes

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