Sodium Hydroxide → 3-[4-(1-Pyrrolidinyl)phenyl]-1-(2,3-dihydro-1H-inden-5-yl)-2-propen-1-one

HRID 1703327Notes

Reaction equation

HRID 1703327 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10](=[O:12])[CH3:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[N:13]1([C:18]2[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1.[OH-].[Na+]>CO>[N:13]1([C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[CH:11][C:10]([C:6]3[CH:5]=[C:4]4[C:9](=[CH:8][CH:7]=3)[CH2:1][CH2:2][CH2:3]4)=[O:12])=[CH:20][CH:19]=2)[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1040374-(1-Pyrrolidinyl)benzaldehydeHCID 2339761-(2,3-Dihydro-1H-inden-5-yl)ethan-1-one

Product 1

HCID 537345213-[4-(1-Pyrrolidinyl)phenyl]-1-(2,3-dihydro-1H-inden-5-yl)-2-propen-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.47 g (9.14 mmoles) of 5, 1.60 g (9.14 mmoles) of p-pyrrolidinylbenzaldehyde and two pellets of sodium hydroxide (about 0.4 g) in 20 ml of methanol was stirred under nitrogen at room temperature for 112 hr. The reaction mixture was cooled in an ice bath and the precipitated solid 3-[4-(1-pyrrolidinyl)phenyl]-1-(2,3-dihydro-1H-inden-5-yl)-2-propen-1-one was filtered and washed with cold methanol. Yield: 1.2 g (41%); m.p. 162° to 164°. Evaporation of the filtrate gave a residue which was dissolved in methanol-toluene (9:1). The solution was filtered, evaporated to 100 ml, and cooled. The precipitated product was collected by filtration and washed with cold methanol. Yield: 0.9 g (31%); m.p. 177° to 179°. λmax (EtOH): 275 nm (ε=16,600); 328 nm (4170); 425 nm (37,800). Calcd for C 22 H23NO: C, 83.24; H, 7.30; N, 4.41. Found: C, 82.99; H, 7.49; N, 4.32.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationthe precipitated solid 3-[4-(1-pyrrolidinyl)phenyl]-1-(2,3-dihydro-1H-inden-5-yl)-2-propen-1-one was filtered
  3. washwashed with cold methanol
  4. customEvaporation of the filtrate
  5. customgave a residue which
  6. filtrationThe solution was filtered
  7. customevaporated to 100 ml
  8. temperaturecooled
  9. filtrationThe precipitated product was collected by filtration
  10. washwashed with cold methanol

Sources & evidence

ORD record
ord-a7c958eb941e4cdea98a3948a4b459c7
Source dataset
uspto-grants-1982_09
Patent number
US04351893

Reaction notes

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