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

HRID 36442
Notes
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Reaction equation

HRID 36442 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+].O>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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 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 702
Ethanol
Solvent

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. additionwas added to the residue
  7. extractionThe aqueous mixture was extracted with ether
  8. customthe organic layer was separated
  9. extractionThe aqueous layer was extracted with ether
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customthe residue was recrystallized

Sources & evidence

ORD record
ord-52c449ca1bc84ea98aa4feae94779a02
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05413997

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes