Cyclooctylamine → N-(Cyclooctyl)-2-[bis(4-methoxymethoxyphenyl)methyl]benzylamine

HRID 1196158Notes

Reaction equation

HRID 1196158 reaction equation
[CH:1]1([NH2:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:10][O:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][O:37][CH3:38])=[CH:31][CH:30]=2)[C:21]2[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=2[CH:23]=O)=[CH:16][CH:15]=1.[BH4-].[Na+]>C(O)C>[CH:1]1([NH:9][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[CH:20]([C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][O:11][CH3:10])=[CH:19][CH:18]=2)[C:29]2[CH:30]=[CH:31][C:32]([O:35][CH2:36][O:37][CH3:38])=[CH:33][CH:34]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 2903CyclooctylamineHCID 4311764Sodium borohydrideHCID 199381432-[Bis(4-methoxymethoxyphenyl)methyl]benzaldehyde

Product 1

HCID 19938097N-(Cyclooctyl)-2-[bis(4-methoxymethoxyphenyl)methyl]benzylamineYield 89.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 50 ml of ethanol was dissolved 0.69 g of cyclooctylamine. To the solution was added 1.96 g of 2-[bis(4-methoxymethoxyphenyl)methyl]benzaldehyde obtained by Reference Example 7, and the mixture was stirred overnight. Then, 0.85 g of sodium borohydride was added thereto, and the reaction mixture was stirred for 2 hours. Thereafter, the solvent was evaporated under reduced pressure, and water was added to the residue. The aqueous mixture was extracted with chloroform, and the organic layer was separated. The aqueous layer was extracted with chloroform, and the organic layer was combined and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography to afford 2.25 g of the desired product (Compound 77) as an oily matter.

Workup

  1. customobtained by Reference Example 7
  2. stirringthe reaction mixture was stirred for 2 hours
  3. customThereafter, the solvent was evaporated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionThe aqueous mixture was extracted with chloroform
  6. customthe organic layer was separated
  7. extractionThe aqueous layer was extracted with chloroform
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5986392dfbe84a28a1b530e2968d4d6a
Source dataset
uspto-grants-1992_05
Patent number
US05112867

Reaction notes

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