Ammonium Chloride → 2-(1-Phenyl-cyclohexyl)-acetamidine

HRID 2169291Notes

Reaction equation

HRID 2169291 reaction equation
[NH4+:1].[Cl-].C[Al](C)C.[C:7]1([C:13]2([CH2:19][C:20]#[N:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[C:7]1([C:13]2([CH2:19][C:20]([NH2:1])=[NH:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 3279092-(1-Phenylcyclohexyl)acetonitrileHCID 16682925Trimethylaluminum

Product 1

HCID 867259372-(1-Phenyl-cyclohexyl)-acetamidineYield 79.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6212ChloroformSolvent

Procedure

To a suspension of NH4Cl (2.34 g, 43.65 mmol) in toluene (20.0 mL) was added drop-wise a solution of trimethyl aluminium (3.15 g, 43.65 mmol, 2M in toluene) at 0° C. The reaction mixture was warmed to room temperature and stirred for 2 h prior to the addition of a solution of (1-phenyl-cyclohexyl)-acetonitrile (253) (2.9 g, 14.55 mmol) in toluene (10.0 mL). The resulting solution was heated to 80° C. for 16 h. The cooled reaction mixture was poured into a slurry of silica-gel (10.0 g) in CHCl3 (20.0 mL) followed by vigorous stirring for 30 min. The silica gel was filtered off and the cake was rinsed in turn with methanol. The solvent was evaporated and the crude product was taken up in 10% methanol in dichloromethane (200.0 mL) and stirred for 30 min. The solid suspension was removed by filtration and the filtrate was evaporated. The crude product was triturated in diethyl ether and the solid was collected by filtration and dried under vacuum to afford HCl-salt of 2-(1-phenyl-cyclohexyl)-acetamidine (254) (2.5 g, 68.0%) as a white solid.

Workup

  1. temperatureThe resulting solution was heated to 80° C. for 16 h
  2. customThe cooled reaction mixture
  3. stirringby vigorous stirring for 30 min
  4. filtrationThe silica gel was filtered off
  5. washthe cake was rinsed in turn with methanol
  6. customThe solvent was evaporated
  7. stirringstirred for 30 min
  8. customThe solid suspension was removed by filtration
  9. customthe filtrate was evaporated
  10. customThe crude product was triturated in diethyl ether
  11. filtrationthe solid was collected by filtration
  12. customdried under vacuum

Sources & evidence

ORD record
ord-9004650a1d3e41c5ba8911a5a4909e84
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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