Triethylamine → 2-[3-(Cyclopentyloxy)-4-methoxyphenyl]-4-phenylbut-3-yn-1-amine--hydrogen chloride (1/1)

HRID 1637113Notes

Reaction equation

HRID 1637113 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16]C(O)=O)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.CC[N:30](CC)CC.[Cl:35]C(OCC)=O.[N-]=[N+]=[N-].[Na+]>O>[ClH:35].[NH2:30][CH2:16][CH:15]([C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=1)[C:20]#[C:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 15463366HCID 15463366, compound

Product 1

HCID 573652252-[3-(Cyclopentyloxy)-4-methoxyphenyl]-4-phenylbut-3-yn-1-amine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenylethynylpropionic acid (1.2 g, 3.3 mmol) in Me2CO (40 ml) was cooled to -15° and treated with Et3N (0.505 ml, 3.63 mmol) and then ethyl chloroformate (0.35 ml, 3.63 mmol), at such a rate so the temperature did not exceed -10°. The mixture was stirred at 0° for 15 minutes. A solution of NaN3 (470 mg, 7.25 mmol) in H2O (2 ml) was added dropwise to the cold solution, and stirring continued in the cold for 15 minutes. The reaction was diluted with H2O, and extracted with Et2O. The extracts were washed with H2O, and dried. The ether extract was slowly added to C6H5Me (100 ml) at 110°, and the solution was heated at 110° for 30 minutes, and the solvent was evaporated. The residue was dissolved in a mixture of dioxane (5 ml), H2O (3 ml), and conc. HCl (3 ml), refluxed for 10 minutes, cooled and the solid filtered. Recrystallization from a mixture of i-propanol and Et2O gave the titled compound as the HCl salt, 1.03 g (84%). mp 212-215°. NMR.

Workup

  1. customdid not exceed -10°
  2. stirringstirring
  3. customcold for 15 minutes
  4. extractionextracted with Et2O
  5. washThe extracts were washed with H2O
  6. customdried
  7. extractionThe ether extract
  8. additionwas slowly added to C6H5Me (100 ml) at 110°
  9. temperaturethe solution was heated at 110° for 30 minutes
  10. customthe solvent was evaporated
  11. dissolutionThe residue was dissolved in a mixture of dioxane (5 ml), H2O (3 ml), and conc. HCl (3 ml)
  12. temperaturerefluxed for 10 minutes
  13. temperaturecooled
  14. filtrationthe solid filtered
  15. customRecrystallization
  16. additionfrom a mixture of i-propanol and Et2O

Sources & evidence

ORD record
ord-1a4cc7c020294f79be0d0d7c920334cc
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

Loading…