Benzylamine → Benzyl-(3-methoxy-4-nitro-benzyl)amine

HRID 1821795Notes

Reaction equation

HRID 1821795 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:6]Br.C(N(CC)CC)C.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([NH:28][CH2:6][C:5]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 126216043-Methoxy-4-nitrobenzyl bromide

Product 1

HCID 22046378Benzyl-(3-methoxy-4-nitro-benzyl)amineYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 150 mL round bottomed flask containing 1.97 g (8.0 mmol) of 3-methoxy-4-nitro-benzyl bromide in 20 mL THF was added, 2.4 g (24 mmol, 3 eq.) of triethylamine followed by 2.5 g (24 mmol, 3 eq.) of benzylamine. The mixture was stirred at room temperature for 2 h, and was then partitioned between 50 mL ethyl acetate and brine. The organic phase was dried over MgSO4 and concentrated. The residue was purified by flash chromatography, eluting with 14% MeOH in dichloromethane to give 1.6 g (73%) of the benzyl amine as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.84 (d, J=8.61 Hz, 1H), 7.34 (m, 5H), 7.16 (s, 1H), 6.99 (d, J=8.61 Hz, 1H), 3.97 (s, 3H), 3.86 (s, 2H), 3.81 (s, 2H).

Workup

  1. additionwas added
  2. customwas then partitioned between 50 mL ethyl acetate and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 14% MeOH in dichloromethane

Sources & evidence

ORD record
ord-663cbb0157e547ae98bd86dd638b58f0
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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