Cyclohexylamine → HCID 525618, compound

HRID 223318Notes

Reaction equation

HRID 223318 reaction equation
[Cl-].Cl[C:3](=[N+:10]([CH3:12])[CH3:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:13]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(Cl)Cl>[CH:13]1([N:19]=[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:10]([CH3:12])[CH3:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 10954662Methanaminium, N-(chlorophenylmethylene)-N-methyl-, chloride

Product 1

HCID 525618HCID 525618, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of (α-chlorobenzylidene)dimethylammonium chloride in methylenechloride described in Example 1, there was added dropwise, a solution of 49.6 g (0.5 mole) of cyclohexylamine in 100 ml of methylenechloride. The temperature of the ensuing exothermal reaction rose from 24.5° to 42.5° C. thus keeping the solvent in reflux. After the reaction subsided, the reaction mixture, consisting of a slurry of white solids in a pale yellow solution, was heated to reflux with stirring. After standing overnight, the slurry was filtered, and the solution was stripped of the solvent and the oily residue distilled. The novel amidine (also called N'-cyclohexyl-N,N-dimethylbenzenecarboximidamide) was obtained as a colorless oil, boiling between 78° and 79° C. at 0.04 mm of mercury pressure and having a refractive index of nD 21.6, 1.5400, in 56.0 g corresponding to a 49% yield. Proton nmr infrared and elemental analysis confirmed its proposed structure.

Workup

  1. additionwas added dropwise
  2. customThe temperature of the ensuing exothermal reaction
  3. customrose from 24.5° to 42.5° C.
  4. temperaturein reflux
  5. temperaturewas heated
  6. temperatureto reflux
  7. filtrationthe slurry was filtered
  8. distillationthe oily residue distilled

Sources & evidence

ORD record
ord-71d6fecc53b142e4bf090a1a1c596bf6
Source dataset
uspto-grants-1982_10
Patent number
US04353830

Reaction notes

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