Triethylamine → 3-Nitro-4-(pyrrolidin-1-ylmethyl)benzonitrile

HRID 659161Notes

Reaction equation

HRID 659161 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C(Cl)Cl>[N+:11]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[CH2:2][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7]#[N:8])([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 219055094-(Bromomethyl)-3-nitrobenzonitrile

Product 1

HCID 666329773-Nitro-4-(pyrrolidin-1-ylmethyl)benzonitrileYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(bromomethyl)-3-nitrobenzonitrile (5.12 g, 21.57 mmol) and pyrrolidine (1.84 g, 25.88 mmol) in CH2Cl2 (72 mL) was added triethylamine (6.54 g, 64.71 mmol) dropwise at 0° C. The mixture was stirred at room temperature for 1.5 h and evaporated to dryness under reduced pressure. The residue was diluted with water (30 mL) and extracted with CH2Cl2 (3×100 mL). The CH2Cl2 solution was dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using a mixture of EtOAc and hexane as eluent to give 3-nitro-4-(pyrrolidin-1-ylmethyl)benzonitrile (2.24 g, 45%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 8.16 (d, 1 H, J=1.6 Hz), 7.94 (br d, 1H, J=8.0 Hz), 7.83 (dd, 1H, J=8.0, 1.6 Hz), 3.99 (s, 2H), 2.54 (br s, 4H), 1.79 (m, 4H).

Workup

  1. customevaporated to dryness under reduced pressure
  2. additionThe residue was diluted with water (30 mL)
  3. extractionextracted with CH2Cl2 (3×100 mL)
  4. dry with materialThe CH2Cl2 solution was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by MPLC on silica gel using
  8. additiona mixture of EtOAc and hexane as eluent

Sources & evidence

ORD record
ord-9f46e4b281b9401da7707cff1860294f
Source dataset
uspto-grants-2011_12
Patent number
US08080568B1

Reaction notes

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