Tetrahydrofuran → (4-Bromo-phenyl)-(2-pyrrolidin-1-yl-ethyl)-amine

HRID 1472817Notes

Reaction equation

HRID 1472817 reaction equation
O1CCCC1.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=O)[CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:9][CH:8]=1>CO>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 1091709N-(4-bromophenyl)-2-(pyrrolidin-1-yl)acetamide

Product 1

HCID 59589763(4-Bromo-phenyl)-(2-pyrrolidin-1-yl-ethyl)-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1M solution of BH3 in tetrahydrofuran (7.7 ml, 7.7 mmol) was added dropwise to N-(4-bromo-phenyl)-2-pyrrolidin-1-yl-acetamide (0.22 g, 0.77 mmol) and the solution was stirred overnight at reflux then subsequently hydrolysed by slow addition of excess of methanol and refluxing for a further 2 hours. The solvent was removed under reduced pressure and aqueous ammonium chloride was added. The aqueous was extracted twice with ethyl acetate and the organics were combined, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the desired product. Yield 0.18 g, 86%. LCMS method: 2, RT: 4.62 min; MI: 267-269 [M+1].

Workup

  1. temperatureat reflux
  2. temperaturerefluxing for a further 2 hours
  3. customThe solvent was removed under reduced pressure and aqueous ammonium chloride
  4. additionwas added
  5. extractionThe aqueous was extracted twice with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac282202587745d2b294541337581cb2
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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