Tetrahydrofuran → HCID 24696530, compound

HRID 1191016Notes

Reaction equation

HRID 1191016 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[CH:11]([NH:14][CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C.C1COCC1>O.CCOC(C)=O>[CH3:15][N:14]([CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)[CH:11]([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 78485N-MethylisopropylamineHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 24696530HCID 24696530, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 4-bromomethyl-benzonitrile (784 mg, 4 mmol) to a stirring mixture of N-isopropyl-methylamine (730 mg, 10 mmol), triethylamine (1.4 mL, 10 mmol) and THF (20 mL) at room temperature, and stir for 12 h. Dilute the mixture with water and EtOAc. Extract the aqueous layer with EtOAc and wash the organic phase with water and brine. Dry the organic solution over Na2SO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel (12 g) eluting with a gradient of DCM to 9:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the desired compound (660 mg, 88%). MS (APCI+) m/z: 189 (M+H)+.

Workup

  1. extractionExtract the aqueous layer with EtOAc
  2. washwash the organic phase with water and brine
  3. dry with materialDry the organic solution over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel (12 g)
  7. washeluting with a gradient of DCM to 9:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

Sources & evidence

ORD record
ord-f2b80d2d4c284b7291564fc1a1d7a9b3
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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