Water → 4-Pyrrolidin-1-yl-3-(thiophen-2-yl)-benzaldehyde

HRID 10628Notes

Reaction equation

HRID 10628 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[C:10]1[S:11][CH:12]=[CH:13][CH:14]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O>[N:15]1([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=2[C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 167688744-Fluoro-3-(thiophen-2-yl)benzaldehyde

Product 1

HCID 219810554-Pyrrolidin-1-yl-3-(thiophen-2-yl)-benzaldehydeYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ex-20B: A solution of 4-fluoro-3-(thiophen-2-yl)-benzaldehyde (1.11 g, 5.38 mmol) from Ex-20A and pyrrolidine (13.0 g, 183.0 mmol) in dimethylformamide (30 mL) was treated with solid K2CO3 (1.7 g, 12.3 mmol), and the resulting mixture was stirred at reflux for 1 week. Upon cooling to room temperature, the reaction was poured into water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic phase was dried over magnesium sulfate, and the solvent was removed under reduced pressure. Silica gel chromatography (hexane/ethyl acetate, 2:1) gave 400 mg (29%) of the desired 4-pyrrolidin-1-yl-3-(thiophen-2-yl)-benzaldehyde product as a yellow oil. 1H-NMR (300 MHz, CDCl3) δ 9.75 (s, 1H), 7.71–7.74 (m, 2H), 7.30 (dd, 1H, J=5.1 and 1.6 Hz), 7.02 (dd, 1H, J=5.1 and 3.7 Hz), 6.96 (m, 1H), 6.81 (d, 1H, J=10.1 Hz), 3.15 (m, 4H), 1.84 (m, 4H).

Workup

  1. temperatureat reflux for 1 week
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b5f1fe8613fa4da4a8336dfb85be8fde
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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