Methylamine → cis N-methyl-4-(2-fluoro-5-bromobenzyloxy)but-2-enylamine

HRID 1066855Notes

Reaction equation

HRID 1066855 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:3]=1[CH2:4][O:5][CH2:6][CH:7]=[CH:8][CH2:9]Br.[CH3:16][NH2:17]>O1CCCC1>[CH3:16][NH:17][CH2:9]/[CH:8]=[CH:7]\[CH2:6][O:5][CH2:4][C:3]1[CH:11]=[C:12]([Br:15])[CH:13]=[CH:14][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 539384814-(2-Fluoro-5-bromobenzyloxy)but-2-enyl bromide

Product 1

HCID 59958653cis N-methyl-4-(2-fluoro-5-bromobenzyloxy)but-2-enylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 250 ml flask 4-(2-fluoro-5-bromobenzyloxy)but-2-enyl bromide (1.968 g, 5.89 mmol) was dissolved in dry tetrahydrofuran (40 5 ml). To this solution methylamine (29.5 ml, 58.9 mmol) was added in one portion and the resulting mixture was stirred at ambient temperature for five hours. The progress of the reaciton was monitored by thin layer chromatography. The solvents were removed in vacuo and the residue was taken up in 1 M potassium carbonate and extracted thrice with methylene chloride. The organic fractions were combined, and dried over sodium sulfate. The solvents were removed in vacuo. The desired title intermediate was further purified by liquid chromatography.

Workup

  1. customThe solvents were removed in vacuo
  2. extractionextracted thrice with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. customThe solvents were removed in vacuo
  5. customThe desired title intermediate was further purified by liquid chromatography

Sources & evidence

ORD record
ord-730a0feaaad94f4e99d6c72420dead5f
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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