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

HRID 1054365Notes

Reaction equation

HRID 1054365 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 1 M 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-4fa8eac5e29e46469008d06ef3bcbe3a
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

Loading…