Dimethylformamide → 4-(1-Pyrrolidinyl)benzaldehyde

HRID 1769939Notes

Reaction equation

HRID 1769939 reaction equation
O=P(Cl)(Cl)Cl.[C:6]1([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN([CH:20]=[O:21])C>>[CH:20]([C:9]1[CH:10]=[CH:11][C:6]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:7][CH:8]=1)=[O:21]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 777261-Phenylpyrrolidine

Product 1

HCID 1040374-(1-Pyrrolidinyl)benzaldehyde

Procedure

POCl3 (6.13 g) was added to stirred DMF (7 ml) at 0° C. and the mixture was stirred for 30 minutes at room temperature. The mixture was added dropwise to a solution of 1-phenylpyrrolidine (5.0 g) in DMF (30 ml) at 0° C. and the resulting solution was stirred overnight at room temperature. The reaction mixture was poured into an ice water mixture and extracted with Et2O. The Et2O layer was washed with saturated NaCl solution, dried over MgSO4 and the solution was concentrated in vacuo. The resulting crystalline mass was washed with Et2O-hexane, yielding 1-(4-formylphenyl)pyrrolidine (3.28 g). ##STR6##

Workup

  1. stirringthe resulting solution was stirred overnight at room temperature
  2. extractionextracted with Et2O
  3. washThe Et2O layer was washed with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationthe solution was concentrated in vacuo
  6. washThe resulting crystalline mass was washed with Et2O-hexane

Sources & evidence

ORD record
ord-401c04d247814cb7902936ad8f7cf9c5
Source dataset
uspto-grants-1995_01
Patent number
US05384320

Reaction notes

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