Allyl bromide → HCID 59104141, compound

HRID 899382Notes

Reaction equation

HRID 899382 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[CH:11](N(C(C)C)CC)([CH3:13])[CH3:12].[CH2:20](Br)[CH:21]=[CH2:22]>C1(C)C=CC=CC=1>[CH2:13]([N:10]([CH2:22][CH:21]=[CH2:20])[C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:9])[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 853000(R)-4-bromo-alpha-methylbenzylamine

Product 1

HCID 59104141HCID 59104141, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2.0 g (10.0 mmol) (R)-1-(4-bromo-phenyl)-ethylamine and 30 ml toluene (dry) was cooled to 0° C. Thereafter, 5.2 ml (30.0 mmol) of di-iso-propylethylamine was added drop-wise, followed by the addition of 7.4 ml (85 mmol) allyl bromide. The resulting mixture was warmed to room temperature and then heated to 95° C. for 2.5 hours. The mixture was filtered. The precipitate was then washed with toluene and the filtrate and washings were combined and then concentrated in vacuo to give a reddish-brown oil. Chromatography on silica gel using 15% ethyl acetate/hexanes gave 2.76 g (99%) oil.

Workup

  1. temperatureThe resulting mixture was warmed to room temperature
  2. temperatureheated to 95° C. for 2.5 hours
  3. filtrationThe mixture was filtered
  4. washThe precipitate was then washed with toluene
  5. concentrationconcentrated in vacuo
  6. customto give a reddish-brown oil

Sources & evidence

ORD record
ord-d39aea3da972403a8d4687d9589fc533
Source dataset
uspto-grants-2008_04
Patent number
US07354941B2

Reaction notes

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