Bromoacetonitrile → 2-((4-Methoxybenzyl)amino)acetonitrile

HRID 1752590Notes

Reaction equation

HRID 1752590 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.Br[CH2:12][C:13]#[N:14]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][CH2:12][C:13]#[N:14])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 11534BromoacetonitrileHCID 754524-Methoxybenzylamine

Product 1

HCID 99897602-((4-Methoxybenzyl)amino)acetonitrileYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of TEA (55.9 ml, 401 mmol), (4-methoxyphenyl)methanamine (50 g, 364 mmol) and 2-bromoacetonitrile (43.7 g, 364 mmol) in THF (500 ml) was stirred at about 10° C. for about 12 h in a 500 ml round-bottomed flask. The reaction was filtered through a pad of silica gel. The crude material was deposited onto silica gel, loaded onto a silica gel column and eluted with Hex/EtOAc (1:1) to afford the title compound (49 g, 278 mmol, 76% yield). 1H-NMR (CDCl3, 400 MHz): δ=3.55 (s, 2H), 3.81 (s, 3H), 3.87 (s, 2H), 6.88 (d, 2H, J=8.4 Hz), 7.26 (d, 2H, J=8.0 Hz)

Workup

  1. filtrationThe reaction was filtered through a pad of silica gel
  2. washeluted with Hex/EtOAc (1:1)

Sources & evidence

ORD record
ord-8f4b9b68f17c4005b81569c65bb257ad
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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