Cyclooctylamine → 2-[Bis(4-benzyloxyphenyl)methyl]-N-(cyclooctyl)benzylamine

HRID 1196159Notes

Reaction equation

HRID 1196159 reaction equation
[CH:1]1([NH2:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:35][CH:34]=2)[C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH:27]=O)=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[BH4-].[Na+]>C(O)C>[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:33]2[CH:34]=[CH:35][C:36]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:37][CH:38]=2)[C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH2:27][NH:9][CH:1]2[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:20][CH:19]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 2903CyclooctylamineHCID 4311764Sodium borohydrideHCID 199380912-[Bis-(4-benzyloxyphenyl)methyl]benzaldehyde

Product 1

HCID 199381232-[Bis(4-benzyloxyphenyl)methyl]-N-(cyclooctyl)benzylamineYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 50 ml of ethanol was dissolved 3 g of cyclooctylamine. To the solution was added 11.41 g of 2-[bis-(4-benzyloxyphenyl)methyl]benzaldehyde obtained by Reference Example 8, and the mixture was heated under reflux for 2 hours. Thereafter, 1.78 g of sodium borohydride was added thereto, and the mixture was heated under reflux for 2 hours. The solvent was evaporated under reduced pressure, and water was added to the residue. The aqueous mixture was extracted with ether, and the organic layer was separated. The aqueous layer was extracted with ether, and then the organic layers were combined and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized to afford 9.19 g of the desired product (Compound 82).

Workup

  1. customobtained by Reference Example 8
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 2 hours
  6. customThe solvent was evaporated under reduced pressure, and water
  7. additionwas added to the residue
  8. extractionThe aqueous mixture was extracted with ether
  9. customthe organic layer was separated
  10. extractionThe aqueous layer was extracted with ether
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customthe residue was recrystallized

Sources & evidence

ORD record
ord-ffef6c703d9a406f84a7b5ed4219173d
Source dataset
uspto-grants-1992_05
Patent number
US05112867

Reaction notes

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