Triethylamine → trans-N-[2-(Dimethylamino)cyclohexyl]-p-nitro-benzamide

HRID 866457Notes

Reaction equation

HRID 866457 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13]([N:15]([CH2:18]C)[CH2:16][CH3:17])C>>[CH3:18][N:15]([CH3:13])[C@@H:16]1[CH2:17][CH2:7][CH2:6][CH2:5][C@H:4]1[NH:1][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chloride2×

Product 1

HCID 54037439trans-N-[2-(Dimethylamino)cyclohexyl]-p-nitro-benzamide

Procedure

This titled amide was prepared from the trans-diamine and 4-nitrobenzoylchloride according to general procedure B using p-nitrobenzoylchloride (1.86 g.; 0.01 mole), the diamine (1.42 g.; 0.01 mole) and triethylamine (1.01 g.; 0.01 mole). The crude oil was crystallized from ether-petroleum ether (30°-60°); 2.232 g. (77% yield) of yellow needles, m.p. 103°-104°. The analytical sample melted at 102°-103°. uv sh 215 nm (ε 2,000); λmax 266 (11,800). ir NH 3380, 3320; N-alkyl 2780; C=O 1645; C=C 1605, 1595; amide II/NO2 /C=C 1535, 1525, 1485, 1350; aromatic 870, 845, 720, nmr in CDCl3 and 100 MHz was in accord. Mass spectrum M+ 291.

Workup

  1. customThe crude oil was crystallized from ether-petroleum ether (30°-60°)

Sources & evidence

ORD record
ord-e8e1fe7d1ba54b5380aa6dc3ff554ea6
Source dataset
uspto-grants-1978_07
Patent number
US04098904

Reaction notes

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