Sodium Hydroxide → 3-[4-(1-Pyrrolidinyl)phenyl]-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-2-propen-1-one

HRID 1703324Notes

Reaction equation

HRID 1703324 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH2:9][CH2:8][CH2:7]2)(=[O:3])[CH3:2].[N:14]1([C:19]2[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1.[OH-].[Na+]>C(O)C>[N:14]1([C:19]2[CH:26]=[CH:25][C:22]([CH:23]=[CH:2][C:1]([C:4]3[CH:13]=[CH:12][C:11]4[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=4[CH:5]=3)=[O:3])=[CH:21][CH:20]=2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 698856-AcetyltetralinHCID 1040374-(1-Pyrrolidinyl)benzaldehyde

Product 1

HCID 538766173-[4-(1-Pyrrolidinyl)phenyl]-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-2-propen-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.6 g of 1 (15 mmol), 2.6 g of p-pyrrolidinylbenzaldehyde (15 mmol), and 0.66 g of sodium hydroxide in 100 ml of ethanol was stirred under nitrogen at 50° for 24 hr. The reaction mixture was cooled in an ice bath, and the precipitated yellow solid 3-[4-(1-pyrrolidinyl)phenyl]-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-2-propen-1-one was collected by filtration and washed with cold ethanol. Yield: 3.2 g (64%); m.p. 167° to 169°. λmax (CHCl3): 420 nm (ε=36,800); 330 nm (4,300); 276 nm (16,400). Calcd for C23H25NO: C, 83.34; H, 7.60; N, 4.23. Found: C, 82.68, 82.67; H, 7.57, 7.55; N, 4.03, 4.15.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationthe precipitated yellow solid 3-[4-(1-pyrrolidinyl)phenyl]-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-2-propen-1-one was collected by filtration
  3. washwashed with cold ethanol

Sources & evidence

ORD record
ord-f5eafef7c1cf4fc6a9226ca041ccdb7f
Source dataset
uspto-grants-1982_09
Patent number
US04351893

Reaction notes

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