1-Phenyl-1-[4-(1-piperidinyl)phenyl]-2-propyn-1-ol, 97% → HCID 9827974, compound

HRID 1935298Notes

Reaction equation

HRID 1935298 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:7]=[C:6]2[OH:17].[C:19]1([C:25]([C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:31][CH:30]=2)(O)[C:26]#[CH:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH3:18][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]2[C:10]([CH:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[C:7]3[CH:27]=[CH:26][C:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)([C:29]4[CH:34]=[CH:33][C:32]([N:35]5[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]5)=[CH:31][CH:30]=4)[O:17][C:6]=32)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 155368351-Phenyl-1-[4-(1-piperidinyl)phenyl]-2-propyn-1-ol, 97%HCID 22463772Methyl 6-(dimethylamino)-4-hydroxynaphthalene-2-carboxylate

Product 1

HCID 9827974HCID 9827974, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 6-dimethylamino-4-hydroxy-2-naphthoate (5 mmol) and 1-phenyl-1-(4-piperidinophenyl)prop-2-yn-1-ol (5 mmol) in toluene (60 cm3) containing acidic alumina (Brockrmann 1) (5 g) was refluxed for 90 minutes. The cooled solution was filtered and the alumina residue washed well with ethyl acetate (5×40 cm3). Removal of the dried solvent gave a brown gum which was flash chromatographed using 30% ethyl acetate in hexane as the eluent to give an off-white solid. Recrystallisation from ethyl acetate and hexane gave the title compound (m.p. =155-156.5° C.).

Workup

  1. temperaturewas refluxed for 90 minutes
  2. filtrationThe cooled solution was filtered
  3. washthe alumina residue washed well with ethyl acetate (5×40 cm3)
  4. customRemoval of the dried solvent
  5. customgave a brown gum which
  6. customchromatographed
  7. customto give an off-white solid
  8. customRecrystallisation from ethyl acetate and hexane

Sources & evidence

ORD record
ord-0534750dac1443b48ea89a5883eba720
Source dataset
uspto-grants-2002_05
Patent number
US06387512B1

Reaction notes

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