Pyrrolidine → 1-(4-nitrophenethyl)pyrrolidine

HRID 2236444Notes

Reaction equation

HRID 2236444 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.C([O-])(O)=O.[Na+]>CC#N>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][CH:11]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 792664-Nitrophenethyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 105369011-(4-nitrophenethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Pyrrolidine (3.89 g, 54.8 mmol) is added to a mixture of 8.40 g (36.5 mmol) of 1-(2-bromoethyl)-4-nitrobenzene and 6.14 g (73.0 mmol) of NaHCO3 in 60 mL of CH3CN at 0° C. The mixture is stirred for 0.5 h at 0° C. and then at 25° C. overnight. The reaction is filtered, the insoluble material is washed with CH3CN and the filtrate and wash were combined. Darco is added, the solution is dried (MgSO4) and evaporated to a viscous red oil. Stirring this material with Et2O caused crystallization of the product. It is collected, washed with Et2O and dried in vacuo to give 7.60 g (95%) of a tan hygroscopic solid. 1H NMR (DMSO-d6) δ 8.22 (d, 2H, J=6.57 Hz), 7.62 (d, 2H, J=6.57 Hz), 3.47 (m, 2H), 3.25 (m, 2H), 3.10 (m, 4H), 1.94 (m, 4H); MS (ESI) m/z 221.2 (M+1).

Workup

  1. customat 25° C.
  2. customovernight
  3. filtrationThe reaction is filtered
  4. washthe insoluble material is washed with CH3CN
  5. washthe filtrate and wash
  6. additionDarco is added
  7. dry with materialthe solution is dried (MgSO4)
  8. customevaporated to a viscous red oil
  9. stirringStirring this material with Et2O
  10. customcrystallization of the product
  11. customIt is collected
  12. washwashed with Et2O
  13. customdried in vacuo
  14. customto give 7.60 g (95%) of a tan hygroscopic solid

Sources & evidence

ORD record
ord-1525c9ededdb4cef9cf22e2b59a88435
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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