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Triethylamine → N-[[4-(Tetradecyloxy)phenyl]methyl]benzamide

HRID 1728885
Notes
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Reaction equation

HRID 1728885 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH2:23])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Cl.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30]N=[CH:28][CH:27]=1.[CH2:34](N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:34]=[CH:28][CH:27]=2)=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 117234984-(Tetradecyloxy)benzenemethanamineHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 19015909N-[[4-(Tetradecyloxy)phenyl]methyl]benzamideYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound is prepared by the procedure of Example 116 using 3.0 g of product from Example 99, 2.01 g Of isonicotinoyl chloride hydrochloride, 3.8 g of triethylamine and 100 ml of methylene chloride. The product is purified by chromatography (silica gel: 3.5% methyl alcohol/chloroform) followed by recrystallization from heptane/methanol to give 3.06 g of the desired product as colorless crystals.

Workup

  1. customThe product is purified by chromatography (silica gel: 3.5% methyl alcohol/chloroform)
  2. customfollowed by recrystallization from heptane/methanol

Sources & evidence

ORD record
ord-94d89a48f68c434f9423d93158a5a283
Source dataset
uspto-grants-1994_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05328921

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes