Triethylamine → trans-p-Cyano-N-[2-(dimethylamino)cyclohexyl]-benzamide

HRID 26254

Reaction equation

HRID 26254 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[CH3:12][N:13]([CH3:21])[C@@H:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]1[NH2:20].C(N(CC)CC)C>C(Cl)Cl>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:20][C@@H:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C@H:14]2[N:13]([CH3:21])[CH3:12])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamine

Product 1

HCID 53649711trans-p-Cyano-N-[2-(dimethylamino)cyclohexyl]-benzamideYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The titled amide was prepared according to general procedure B using p-cyanobenzoyl chloride (1.65 g.; 0.01 mole), the trans-2-(dimethylamino)cyclohexylamine (1.42 g.; 0.01 mole) and triethylamine (1.01 g.; 0.01 mole) but using CH2Cl2 for extraction. The crude solid was crystallized from ether to give colorless needles, 1.71 g. (63% yield), m.p. 160°-161°. uv λmax 236 nm (ε 17,900); sh 285 (2,550). ir NH 3320; N-alkyl 2780; C=N 2220; C=O 1635; C=C 1610, 1500; amide II 1550; aromatic 860. NMR in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 271.

Workup

  1. extractionfor extraction
  2. customThe crude solid was crystallized from ether
  3. customto give colorless needles, 1.71 g

Sources & evidence

ORD record
ord-32950554ecca44488d74a21be65e7625
Source dataset
uspto-grants-1979_04
Patent number
US04148914

Linked notes

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