Pyridine → N-(2-Pyridinylmethyl)-4-(tetradecyloxy)benzeneacetamide

HRID 1728836Notes

Reaction equation

HRID 1728836 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.N1C=CC=CC=1.[CH2:15]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37](Cl)=[O:38])=[CH:32][CH:31]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C(Cl)Cl.C(Cl)(Cl)Cl>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][NH:1][C:37](=[O:38])[CH2:36][C:33]1[CH:34]=[CH:35][C:30]([O:29][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 195092-PyridinemethanamineHCID 10021844p-Tetradecyloxyphenylacetylchloride

Product 1

HCID 10365880N-(2-Pyridinylmethyl)-4-(tetradecyloxy)benzeneacetamideYield 61.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 4.64 g of 2-(aminomethyl)pyridine, 13.2 ml of pyridine and 50 ml of methylene chloride is added, dropwise, 15 g of product from Example 53 in 150 ml of methylene chloride. The reaction is stirred at 0° C. for 1 hour followed by 18 hours at room temperature. The reaction is diluted with chloroform, washed with sodium bicarbonate, water and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica ge1:75-100% ethyl acetate/hexane) to give 11.0 g of the desired product as colorless prisms.

Workup

  1. waitfollowed by 18 hours at room temperature
  2. washwashed with sodium bicarbonate, water and saturated sodium chloride
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography (silica ge1:75-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8371e7ff438841bea1f0fb6598dcc403
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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