Pyrrolidine → 2-Pyrrolidin-1-yl-5-thiophen-2-yl-benzaldehyde

HRID 10683Notes

Reaction equation

HRID 10683 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:3]=1[CH:4]=[O:5].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C(OCC)(=O)C>[N:15]1([C:2]2[CH:9]=[CH:8][C:7]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 167686562-Fluoro-5-(thiophen-2-yl)benzaldehyde

Product 1

HCID 219810662-Pyrrolidin-1-yl-5-thiophen-2-yl-benzaldehydeYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ex-63A: A solution of 2-fluoro-5-thiophen-2-yl-benzaldehyde (1.42 g, 6.89 mmol) in pyrrolidine was refluxed (10 mL). After 4.5 days the reaction mixture was cooled and diluted with ethyl acetate. The solution of ethyl acetate was washed with hydrochloric acid (0.5M) sodium carbonate (2M) and saturated solution of sodium bicarbonate, dried over sodium sulfate, and concentrated. The crude product was purified by flash chromatography. Elution with ethyl acetate (20%, v/v, in hexane) afforded 2-pyrrolidin-1-yl-5-thiophen-2-yl-benzaldehyde (0.5 g, 32%). 1H NMR (CDCl3) δ 10.14 (s, 1H), 7.94 (d, J=2 Hz, 1H), 7.62 (dd, J=2.7, 9 Hz, 1H), 7.22–7.20 (m, 2H), 7.07–7.04 (m, 1H), 6.86 (d, J=9 Hz, 1H), 3.41 (m, 4H), 2.01 (m, 4H).

Workup

  1. temperatureAfter 4.5 days the reaction mixture was cooled
  2. washThe solution of ethyl acetate was washed with hydrochloric acid (0.5M) sodium carbonate (2M) and saturated solution of sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography
  6. washElution with ethyl acetate (20%, v/v, in hexane)

Sources & evidence

ORD record
ord-db9d400ae05d48d8a73cef95d7c4ce31
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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