1-Ethynylcyclohexylamine → HCID 12939913, compound

HRID 67120Notes

Reaction equation

HRID 67120 reaction equation
[C:1]([C:3]1[CH:13]=[C:12]([NH:14][C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])[CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH:7]1[O:9][CH2:8]1)#[N:2].[C:20]([C:22]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)#[CH:21]>C(O)C>[C:1]([C:3]1[CH:13]=[C:12]([NH:14][C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])[CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH:7]([OH:9])[CH2:8][NH:28][C:22]1([C:20]#[CH:21])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)#[N:2]

Participants

4

Reactant 2

HCID 1216911-EthynylcyclohexylamineHCID 233181271-[2-Cyano-4-(isobutyroyl-amino)-phenoxy]-2,3-epoxy-propane

Product 1

HCID 12939913HCID 12939913, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.8 gm (0.03 mol) of 1-[2-cyano-4-(isobutyroyl-amino)-phenoxy]-2,3-epoxy-propane were dissolved in 80 ml of ethanol, and after addition of 7.5 gm (0.06 mol) of 1-ethinyl-cyclohexyl-amine the mixture was refluxed for one hour. The solvent was then distilled off, and the residue was acidified with dilute HCl. After extraction with ethyl acetate the aqueous phase was made alkaline by addition of NaOH, whereby basic components precipitated in oily form. They were taken up in ethyl acetate, the organic phase was washed with water, dried over MgSO4, evaporated and the solid residue was recrystallized twice from acetonitrile.

Workup

  1. temperaturewas refluxed for one hour
  2. distillationThe solvent was then distilled off
  3. extractionAfter extraction with ethyl acetate the aqueous phase
  4. additionby addition of NaOH, whereby basic components
  5. customprecipitated in oily form
  6. washthe organic phase was washed with water
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customthe solid residue was recrystallized twice from acetonitrile

Sources & evidence

ORD record
ord-1bc5ffdd6ad2418a94a352058c4ea0a0
Source dataset
uspto-grants-1982_08
Patent number
US04344964

Reaction notes

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