Pyrrolidine → HCID 58424199, compound

HRID 2096637Notes

Reaction equation

HRID 2096637 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=2)[CH:7]=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:2].[C:19]([N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)(=[O:21])[CH3:20].N1CCCC1>CO>[C:19]([N:22]1[CH2:27][CH2:26][C:25]2([CH2:2][C:1](=[O:3])[C:4]3[C:9](=[CH:8][CH:7]=[C:6]([C:11]4[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=4)[C:17]#[N:18])[CH:5]=3)[O:10]2)[CH2:24][CH2:23]1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 122563N-Acetyl-4-piperidoneHCID 23004914HCID 23004914, compound

Product 1

HCID 58424199HCID 58424199, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3′-acetyl-4′-hydroxybiphenyl-3-carbonitrile (0.802 g, 3.38 mmol) and 1-acetylpiperidin-4-one (0.477 g, 3.38 mmol) in MeOH (50 mL) was added pyrrolidine (0.4 mL). The resulting solution was heated to reflux for 1.5 h. The reaction mixture was cool down to room temperature and the solvent was removed under reduced pressure. The residue was dissolved in DCM and washed with aqueous 1 M HCl, aqueous 1 M NaOH, and brine successively. Solvent was removed under reduced pressure after dried over anhydrous Na2SO4, to yield 0.768 g of 3-(1′-acetyl-4-oxospiro[chroman-2,4′-piperidine]-6-yl)benzonitrile as a light brown solid. It was used for next step without further purification. MS ESI +ve m/z 361 (M+H)+.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 1.5 h
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in DCM
  5. washwashed with aqueous 1 M HCl, aqueous 1 M NaOH, and brine successively
  6. customSolvent was removed under reduced pressure
  7. dry with materialafter dried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-5cd006291e36404a9f0c05bf74f3b8f2
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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