Triethylamine → HCID 13239485, compound

HRID 580428Notes

Reaction equation

HRID 580428 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.[Cl:16][C:17]1[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=1)[O:20][CH:21]([CH2:25][CH3:26])[C:22](Cl)=[O:23]>C1(C)C=CC=CC=1>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][NH:1][C:22](=[O:23])[CH:21]([O:20][C:19]1[CH:27]=[CH:28][CH:29]=[C:17]([Cl:16])[CH:18]=1)[CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 13239463HCID 13239463, compound

Product 1

HCID 13239485HCID 13239485, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In 50 ml of toluene were dissolved 1.6 g (0.012 mole) of 2-aminomethylpyridine and 1.2 g (0.012 mole) of triethylamine, and thereto was added dropwise a solution 2.8 g (0.012 mole) of 2-(3-chlorophenoxy)-butyroyl chloride in 20 ml of toluene at room temperature with stirring. After the reaction was carried out for 4 hours, the reaction mixture was washed with water, dilute aqueous sodium hydroxide and then water successively. After the toluene layer was dried, the toluene was removed by distillation. The thus obtained oil was subjected to column chromatography to give 2.3 g of N-(2-pyridylmethyl)-2-(3-chlorophenoxy)-butyramide showing nD26 1.5610 as pale yellow oily liquid.

Workup

  1. washthe reaction mixture was washed with water, dilute aqueous sodium hydroxide
  2. dry with materialAfter the toluene layer was dried
  3. customthe toluene was removed by distillation

Sources & evidence

ORD record
ord-de5c433427a44c0b821196f8df9cdcb6
Source dataset
uspto-grants-1988_06
Patent number
US04753674

Reaction notes

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