Cyclohexaneacetic acid → HCID 20299756, compound

HRID 1733494Notes

Reaction equation

HRID 1733494 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.[CH:12]1([CH2:18][C:19](O)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:19](=[O:20])[CH2:18][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 21363Cyclohexaneacetic acidHCID 748663-Methoxyphenethylamine

Product 1

HCID 20299756HCID 20299756, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

A stirred mixture of 20 g of 3-methoxy-benzeneethanamine and 15.2 g of cyclohexylacetic acid was heated at 190°-200° C. under an inert atmosphere for 45 minutes and was then cooled to 30° C. The product was dissolved in ethyl acetate and the solution was washed successively with N sodium hydroxide solution, N hydrochloric acid and water and was evaporated to dryness. The 29 g of oil residue was crystallized from petroleum ether (b.p.=40°-70° C.) and the product was dried to obtain 21.3 g of N-[2-(3-methoxyphenyl)-ethyl]cyclohexane-acetamide in the form of a white solid melting at 74° C.

Workup

  1. temperaturewas heated at 190°-200° C. under an inert atmosphere for 45 minutes
  2. washthe solution was washed successively with N sodium hydroxide solution, N hydrochloric acid and water
  3. customwas evaporated to dryness
  4. customThe 29 g of oil residue was crystallized from petroleum ether (b.p.=40°-70° C.)
  5. customthe product was dried

Sources & evidence

ORD record
ord-1f1b4f5ef8d040f486bcbcf3bd968e09
Source dataset
uspto-grants-1980_12
Patent number
US04242355

Reaction notes

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