4-Phenoxybenzaldehyde → N-(4-Fluorobenzyl)-N-(4-phenoxybenzyl)amine

HRID 1781173Notes

Reaction equation

HRID 1781173 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1.C([BH3-])#N.[Na+]>CO>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH:22][CH2:12][C:11]2[CH:14]=[CH:15][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 661394-PhenoxybenzaldehydeHCID 673264-FluorobenzylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19069243N-(4-Fluorobenzyl)-N-(4-phenoxybenzyl)amineYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Phenoxybenzaldehyde (1.0 g, 5.0 mmol) and 4-fluorobenzylamine (631 mg, 5.0 mmol) were dissolved in methanol (17 mL) under a nitrogen at room temperature. Sodium cyanoborohydride (317 mg, 5.0 mmol) was added, and stirring was continued for 48 hours. The solvent was evaporated, and the residue was suspended in ether, washed with brine, and dried over Na2SO4. The ether was evaporated, and the crude product was chromatographed on silica gel eluting with 3% methanol in methylene chloride to provide 1.5 g (97%) of the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 1.55 (s, 1H), 3.76 (s, 2H), 3.78 (s, 2H), 6.95-7.15 (m, 7H), 7.25-7.40 (m, 6H). MS (DCl/N H3) m/e 308 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customThe ether was evaporated
  5. customthe crude product was chromatographed on silica gel eluting with 3% methanol in methylene chloride

Sources & evidence

ORD record
ord-ec70a866ca114f8db510886501039075
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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