N-Methylcyclohexylamine → HCID 5050807, compound

HRID 1034281Notes

Reaction equation

HRID 1034281 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[C:16]1([CH3:25])[CH:21]=[CH:20][C:19]([C:22](Cl)=[O:23])=[CH:18][CH:17]=1>C1COCC1>[CH:3]1([N:2]([CH3:1])[C:22](=[O:23])[C:19]2[CH:20]=[CH:21][C:16]([CH3:25])=[CH:17][CH:18]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 7514N-MethylcyclohexylamineHCID 8471TriethylamineHCID 134054-Methylbenzoyl Chloride

Product 1

HCID 5050807HCID 5050807, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold stirred solution of N-methylcylohexylamine (20 ml, 0.15 mol) and triethylamine (22 ml) in dry THF (100 mi) under argon was slowly added p-toluoyl chloride (20 ml, 0.15 mol). A white precipitate formed. The ice bath was removed and the mixture stirred at ambient temperature for 24 h. Ice cold 2M hydrochloric acid (100 ml) was added and the organic layer separated. The aqueous layer was extracted with ethyl acetate (3×100 ml). The combined organics were washed with brine (3×100 ml), dried over Na2SO4, filtered and evaporated to give the crude amide, which was crystallised from hexane to give N-cyclohexyl-N-methyl 4-methylbenzamide (30.9 g, 87%) as a white crystalline solid.

Workup

  1. customA white precipitate formed
  2. customThe ice bath was removed
  3. additionIce cold 2M hydrochloric acid (100 ml) was added
  4. customthe organic layer separated
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×100 ml)
  6. washThe combined organics were washed with brine (3×100 ml)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customto give the crude amide, which
  11. customwas crystallised from hexane

Sources & evidence

ORD record
ord-98ffdfdcfe4b49a9ad4fbaf2d2ed3261
Source dataset
uspto-grants-1994_05
Patent number
US05314880

Reaction notes

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