Water → 1-[(3-Nitrophenyl)methyl]pyrrolidine

HRID 2095205Notes

Reaction equation

HRID 2095205 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(CC)CC)C.O>C1COCC1>[N+:9]([C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31268PyrrolidineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 7828801-[(3-Nitrophenyl)methyl]pyrrolidineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-bromomethyl-3-nitrobenzene (the compound of formula (R), 5 mmol, 1.08 g), pyrrolidine (11 mmol, 0.79 g), and 1.0 mL triethylamine (the compound of formula NRR′R″ wherein R═R′═R″=ethyl) in THF (35 mL) was heated at 60° C. for 1 hour. The reaction mixture was allowed to cool to ambient temperature overnight with stirring. Water was then added to the reaction mixture and the product was extracted into diethyl ether. The ether layer was dried over sodium sulfate, filtered, and evaporated to yield 1.03 g (94%) of 1-(3-nitro-benzyl)-pyrrolidine (the compound of formula (S)) which was used in the following reaction without further purification.

Workup

  1. extractionthe product was extracted into diethyl ether
  2. dry with materialThe ether layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-11359868ee10410487bcc1b937717312
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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