Methanol → HCID 18623251, compound

HRID 324323Notes

Reaction equation

HRID 324323 reaction equation
[C:1]([C:3]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7][CH:6]([NH:9][CH2:10][CH2:11][NH2:12])[CH2:5][CH2:4]1)#N.S(=O)(=O)(O)[OH:20].[CH3:24][OH:25]>>[CH3:24][O:25][C:1]([C:3]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7][CH:6]([NH:9][CH2:10][CH2:11][NH2:12])[CH2:5][CH2:4]1)=[O:20]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 15541197HCID 15541197, compound

Product 1

HCID 18623251HCID 18623251, compoundYield 76%

Conditions

Temperature
82.5 °C

Procedure

A mixture of 2-[4-cyano-4-phenylcyclohexylamino]ethylamine (2.34 g, 10 mmol) and concentrated sulfuric acid (20 mL) was heated at 80-85° C. for 10 hours. It was cooled to room temperature, mixed with anhydrous methanol (200 mL), and refluxed for 20 hours. Solvent was evaporated and the residue was poured onto ice (200 g) and basified to pH 11 by addition of 6 N NaOH. It was extracted with dichloromethane (4×125 mL), dried (potassium carbonate) and solvent evaporated to leave the product as an oil (2.1 g, 76%). This product was a pure mixture of cis and trans isomers. It was used in the next step without any further purification.

Workup

  1. temperatureIt was cooled to room temperature
  2. temperaturerefluxed for 20 hours
  3. customSolvent was evaporated
  4. additionthe residue was poured onto ice (200 g)
  5. additionbasified to pH 11 by addition of 6 N NaOH
  6. extractionIt was extracted with dichloromethane (4×125 mL)
  7. dry with materialdried (potassium carbonate) and solvent
  8. customevaporated

Sources & evidence

ORD record
ord-3fb270fb193a453abec4e848f5e9cd0f
Source dataset
uspto-grants-2001_04
Patent number
US06218390B1

Reaction notes

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