Triethylamine → 4-((Pyrrolidin-1-yl)methyl)benzonitrile

HRID 1191001Notes

Reaction equation

HRID 1191001 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.C(N(CC)CC)C>C1COCC1>[N:1]1([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 49628034-((Pyrrolidin-1-yl)methyl)benzonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add pyrrolidine (0.89 mL, 10.74 mmol) to a stirred solution of 4-bromomethyl-benzonitrile (1 g, 5.1 mmol) and triethylamine (1.5 mL, 10.74 mmol) in anhydrous THF (26 mL). Stir reaction overnight at room temperature. Partition the reaction mixture between EtOAc and water. Extract the aqueous phase twice with EtOAc. Dry the combined organic extracts over MgSO4, filter, and concentrate in vacuo to obtain the desired intermediate (918 mg, 97%) suitable for use without further purification. MS (APCI+) m/z: 187 (M+H)+.

Workup

  1. customreaction overnight at room temperature
  2. customPartition the reaction mixture between EtOAc and water
  3. extractionExtract the aqueous phase twice with EtOAc
  4. dry with materialDry the combined organic extracts over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f51f25de48834a2fb916cb3083796bee
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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