Methanol → HCID 18623251, compound

HRID 1106658Notes

Reaction equation

HRID 1106658 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-phenylcyclohex-1-yl]aminoethylamine (2.34 g, 10 mmol) and concentrated sulfuric acid (20 mL) was heated at 80-85° C. for 10 h. It was cooled to room temperature, mixed with anhydrous methanol (200 mL), and refluxed for 20 h. Solvent was evaporated and the residue was poured onto ice (200 g) and basified to pH 11 by addition 6N 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%). 1H-NMR showed this product to be pure and a 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 h
  3. customSolvent was evaporated
  4. additionthe residue was poured onto ice (200 g)
  5. additionbasified to pH 11 by addition 6N 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-bc48f5f5d3674e759563da4cb7f49557
Source dataset
uspto-grants-2000_05
Patent number
US06057350

Reaction notes

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