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Pyridine → N-[2-(2-Pyridinyl)ethyl]-4-(tetradecyloxy)benzamide

HRID 247967
Notes
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Reaction equation

HRID 247967 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.N1C=CC=CC=1.[CH2:16]([O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(Cl)Cl.C(Cl)(Cl)Cl>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][CH2:2][NH:1][C:35](=[O:36])[C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:39][CH:38]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1049PyridineHCID 759192-PyridineethanamineHCID 9998158Benzoyl chloride, 4-(tetradecyloxy)-

Product 1

HCID 10478314N-[2-(2-Pyridinyl)ethyl]-4-(tetradecyloxy)benzamideYield 41.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent
HCID 6344
Dichloromethane
Solvent
2×

Conditions

Temperature
0 °C

Procedure

To a 0° solution of 2.54 g of 2-(2-aminoethyl)pyridine, 50 ml of methylene chloride and 6.42 ml of pyridine is added, dropwise, 7.0 g of product from Example 3 in 250 ml of methylene chloride. The reaction is stirred at 0° C. for 2 hours followed by 14 hours at room temperature. The reaction is diluted with chloroform, washed with saturated sodium bicarbonate, water and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:75-100% ethyl acetate/hexane) to give 3.58 g of the desired product.

Workup

  1. waitfollowed by 14 hours at room temperature
  2. washwashed with saturated sodium bicarbonate, water and saturated sodium chloride
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography (silica gel:75-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3d766805a00346a79f60fb0a4ee3c4ec
Source dataset
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05208247

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes