HCID 13279982, compound → HCID 20225028, compound

HRID 1249178Notes

Reaction equation

HRID 1249178 reaction equation
[CH:1]1([CH:7]([C:14]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:17][CH2:16][CH2:15]2)[NH:8][C:9](=O)[CH2:10][O:11][CH3:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>O1CCCC1>[CH:1]1([CH:7]([C:14]2([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:15][CH2:16][CH2:17]2)[NH:8][CH2:9][CH2:10][O:11][CH3:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 13279982HCID 13279982, compound

Product 1

HCID 20225028HCID 20225028, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulphide complex (2.48 ml) was added dropwise to a refluxing solution of the acetamide (2.6 g) prepared above in tetrahydrofuran (6 ml). The mixture was heated under reflux for 2 hours left at room temperature for 16 hours and heated under reflux for 2 hours, cooled in ice, and hydrolysed by the slow dropwise addition of ice-water. The mixture was acidified, basified, and extracted with ether. The washed and dried extracts were evaporated to leave an oil which was purified by high pressure liquid chromatography to give N-[(cyclohexyl)(1-phenylcyclobutyl)methyl]-2-methoxyethylamine as a pale yellow oil the physical characteristics of which were not determined.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureheated
  4. temperatureunder reflux for 2 hours
  5. temperaturecooled in ice
  6. extractionextracted with ether
  7. washThe washed
  8. customdried extracts
  9. customwere evaporated
  10. customto leave an oil which
  11. customwas purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-b070ec2e1ec64401b3585a654eca617f
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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