Methylamine → HCID 21196055, compound

HRID 1066822Notes

Reaction equation

HRID 1066822 reaction equation
[NH2:1][CH3:2].[F:3][C:4]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:5]=1[CH2:6][O:7][CH2:8][C:9]#[C:10][CH2:11]Br>O1CCCC1>[CH3:2][NH:1][CH2:11][C:10]#[C:9][CH2:8][O:7][CH2:6][C:5]1[CH:13]=[C:14]([Br:17])[CH:15]=[CH:16][C:4]=1[F:3]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 21195964HCID 21195964, compound

Product 1

HCID 21196055HCID 21196055, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of aminomethane (89 ml of a 2 M solution in tetrahydrofuran, 178 mmol) was added to a solution of 4-(2-fluoro-5-bromobenzyloxy)but-2-ynyl bromide (6.0 g, 17.8 mmol) in tetrahydrofuran (89 ml). The cloudy reaction mixture was stirred for about fifteen minutes, at which time no starting material remained, as determined by thin layer chromatography. The solvents were removed in vacuo. The residue was taken up in methylene chloride and washed with 1 M potassium carbonate. The aqueous phase was back-extracted thrice with methylene chloride. The organic fractions were combined, and dried over sodium sulfate. The solvents were removed in vacuo. The resulting oil was further purified by flash chromatography, affording 4.24 grams (83%) of the title intermediate as a yellow oil.

Workup

  1. customThe cloudy reaction mixture
  2. customThe solvents were removed in vacuo
  3. washwashed with 1 M potassium carbonate
  4. extractionThe aqueous phase was back-extracted thrice with methylene chloride
  5. dry with materialdried over sodium sulfate
  6. customThe solvents were removed in vacuo
  7. customThe resulting oil was further purified by flash chromatography

Sources & evidence

ORD record
ord-2ce0df4d09ad4e03bd30a39dd98da21d
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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