N-Methylcyclohexylamine → HCID 5050807, compound

HRID 327797Notes

Reaction equation

HRID 327797 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 ml) 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 anhydrous sodium sulphate, 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 anhydrous sodium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customto give the crude amide, which
  11. customwas crystallised from hexane

Sources & evidence

ORD record
ord-e156bbd4521a4ef6a8267608fd4b44e1
Source dataset
uspto-grants-1993_12
Patent number
US05274094

Reaction notes

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