Benzylamine → HCID 21195959, compound

HRID 1066823Notes

Reaction equation

HRID 1066823 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:11]=1[CH2:12][O:13][CH2:14][C:15]#[C:16][CH2:17]Br>O1CCCC1>[CH2:1]([NH:8][CH2:17][C:16]#[C:15][CH2:14][O:13][CH2:12][C:11]1[CH:19]=[C:20]([Br:23])[CH:21]=[CH:22][C:10]=1[F:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 21195964HCID 21195964, compound

Product 1

HCID 21195959HCID 21195959, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzylamine (0.98 ml, 8.93 mmol) was added to a solution of 4-(2-fluoro-5-bromobenzyloxy)but-2-ynyl bromide (300 mg, 0.893 mmol) in tetrahydrofuran (4.5 ml). The cloudy reaction mixture was stirred for about twenty hours, 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 with methylene chloride (2×15 ml). 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 200 mg (62%) of the title intermediate.

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 with methylene chloride (2×15 ml)
  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-ab88c965908f44949e23b5c0ffac70df
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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