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

HRID 1957331Notes

Reaction equation

HRID 1957331 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 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-methylene chloride to provide 1.5 g (97%) of the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ1.55 (s, 1H), 3.76 (s, 2H), 3.78 (s, 2H), 6.95-7.15 (m, 7H), 7.25-7.40 (m, 6H). MS (DCl/NH3) 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-methylene chloride

Sources & evidence

ORD record
ord-69ced18a96644c1f9ae14fbe5db46a52
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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