Benzylamine → N-Allylbenzylamine

HRID 2264833Notes

Reaction equation

HRID 2264833 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9](Br)[CH:10]=[CH2:11].C(=O)(O)[O-].[Na+]>CS(C)=O.[I-].[Na+]>[C:2]1([CH2:1][NH:8][CH2:11][CH:10]=[CH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 7841Allyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 521150N-AllylbenzylamineYield 57%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of benzylamine (5.7 ml, 52.2 mmol) and sodium iodide (38 mg, 0.25 mmol) in DMSO (30 ml) was added dropwise allyl bromide (2.2 ml, 25.4 mmol) at 0° C. under argon. After stirring for 3 h at room temperature the reaction was complete as shown by TLC (cyclohexanes:ethyl acetate 1:1). Then saturated aqueous sodium bicarbonate solution was added, the product was extracted with diethyl ether (100 ml) and the organic layer was washed with brine. The crude product was purified via flash chromatography to give the title compound (2.1 g, 57%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.4-7.2 (m, 5H), 6.0-5.9 (m, 1H), 5.3-5.1 (m, 2H), 3.8 (s, 2H), 3.3 (d, 2H), 1.5 (bs, 1H).

Workup

  1. extractionthe product was extracted with diethyl ether (100 ml)
  2. washthe organic layer was washed with brine
  3. customThe crude product was purified via flash chromatography

Sources & evidence

ORD record
ord-076ae1503f5547b4a389c87520b26e94
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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