Triethylamine → 4-[2-(4-Acetyl-3-hydroxy-2-propylphenoxy)-ethoxy]-N-[4-(3-pyridinyl)butyl]benzamide

HRID 652495Notes

Reaction equation

HRID 652495 reaction equation
[C:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)=[C:6]([CH2:23][CH2:24][CH3:25])[C:5]=1[OH:26])(=[O:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.[N:51]1[CH:56]=[CH:55][CH:54]=[C:53]([CH2:57][CH2:58][CH2:59][CH2:60][NH2:61])[CH:52]=1>CN(C=O)C>[C:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([NH:61][CH2:60][CH2:59][CH2:58][CH2:57][C:53]3[CH:52]=[N:51][CH:56]=[CH:55][CH:54]=3)=[O:18])=[CH:19][CH:20]=2)=[C:6]([CH2:23][CH2:24][CH3:25])[C:5]=1[OH:26])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 72927Pyridine, 3-(4-aminobutyl)-HCID 199401P,P-Diphenylphosphinic azideHCID 139128254-[2-(4-Acetyl-3-hydroxy-2-propylphenoxy)ethoxy]benzoic acid

Product 1

HCID 139127964-[2-(4-Acetyl-3-hydroxy-2-propylphenoxy)-ethoxy]-N-[4-(3-pyridinyl)butyl]benzamideYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of 1.22 g of 4-[2-(4-Acetyl-3-hydroxy-2-propylphenoxy)ethoxy]benzoic acid in 15 mL of anhydrous DMF was added to 0.8 mL of diphenylphosphoryl azide and 1.05 mL of anhydrous triethylamine. The resulting mixture was stirred at 0° C. for one hour and then 0.56 g of 3-pyridine butanamine was added. The mixture was stirred in ice bath for 1 hour and at room temperature for 6 hours. The solvent was removed in vacuo, the residue was dissolved in methylene chloride and washed with sodium bicarbonate solution. The extract was dried (over magnesium sulfate) and concentrated in vacuo to an oil which was purified by HPLC using 7% methanol-ethyl acetate to give an oil which was triturated with ethyl acetate-ether and filtered to yield 1.0 g, mp 93° , (60% yield) of 4-[2-(4-Acetyl-3-hydroxy-2-propylphenoxy)-ethoxy]-N-[4-(3-pyridinyl)butyl]benzamide, the title compound.

Workup

  1. stirringThe mixture was stirred in ice bath for 1 hour
  2. waitat room temperature for 6 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washwashed with sodium bicarbonate solution
  6. dry with materialThe extract was dried (over magnesium sulfate)
  7. concentrationconcentrated in vacuo to an oil which
  8. customwas purified by HPLC
  9. customto give an oil which
  10. customwas triturated with ethyl acetate-ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-f25a56064e3b42ed97d9f7b775721828
Source dataset
uspto-grants-1987_06
Patent number
US04672066

Reaction notes

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