Benzylamine → benzyl[(4-methoxyphenyl)methyl]amine

HRID 1686259Notes

Reaction equation

HRID 1686259 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:11]([NH:18][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 312444-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 738564benzyl[(4-methoxyphenyl)methyl]amine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

4-methoxybenzaldehyde (5 g, 35 mmol) and benzylamine (3.8 g, 35 mmol) were added to sodium triacetoxyborohydride (10.4 g, 49 mmol) in dichloroethane (125 mL). The reaction was stirred at ambient temperature 2 hours, then concentrated. The mixture was diluted with dichloromethane (200 mL), washed with saturated aqueous sodium hydrogen carbonate (200 mL), brine (200 mL) and dried over magnesium sulfate. The crude amine was concentrated and purified by silica gel chromatography (70% ethyl acetate in hexanes) To afford N-benzyl-1-(4-methoxyphenyl)methanamine as an oil. 1H NMR (400 MHz, DMSO-d6): δ, ppm: 3.59 (s, 2H), 3.64 (s, 2H), 3.71 (s, 3H), 6.86 (d, J=8.8 Hz, 2H), 7.28 (m, 7H).

Workup

  1. concentrationconcentrated
  2. additionThe mixture was diluted with dichloromethane (200 mL)
  3. washwashed with saturated aqueous sodium hydrogen carbonate (200 mL), brine (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe crude amine was concentrated
  6. custompurified by silica gel chromatography (70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9ede491d48bc4bd68f72eff2d2a47f25
Source dataset
uspto-grants-2012_04
Patent number
US08148544B2

Reaction notes

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