Water → 4-(2-pyrrolidin-1-ylethoxy)benzaldehyde

HRID 703526Notes

Reaction equation

HRID 703526 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N:13]1([CH2:2][CH2:3][O:4][C:5]2[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 2627064-(2-Bromoethoxy)Benzaldehyde

Product 1

HCID 9768444-(2-pyrrolidin-1-ylethoxy)benzaldehydeYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.29 g of 4-(2-bromoethoxy)benzaldehyde, 1.42 g of pyrrolidine and 2.07 g of potassium carbonate in 8 ml of N,N-dimethylformamide was stirred at 60° C. for 2 hours. After cooling, water was added and the whole was extracted with ethyl acetate. The ethyl acetate layer was extracted with aqueous hydrochloric acid. The aqueous layer was made alkaline with potassium carbonate and extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The residue was distilled to give 1.72 g of colorless oil, b.p. 170° C. (5 mmHg).

Workup

  1. temperatureAfter cooling
  2. extractionthe whole was extracted with ethyl acetate
  3. extractionThe ethyl acetate layer was extracted with aqueous hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-ecd9103d650245a79522e38e7d2fde7d
Source dataset
uspto-grants-1991_01
Patent number
US04983633

Reaction notes

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