Water → HCID 68513562, compound

HRID 1717273Notes

Reaction equation

HRID 1717273 reaction equation
[N:1]([C:4]1[CH:20]=[CH:19][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].O=[C:22]([CH2:29][CH2:30][CH3:31])[CH2:23][C:24]([O:26]CC)=[O:25].[O-]CC.[Na+].O>C(O)C>[N:13]1([CH2:12][CH2:11][NH:10][C:8]([C:7]2[CH:6]=[CH:5][C:4]([N:1]3[C:22]([CH2:29][CH2:30][CH3:31])=[C:23]([C:24]([OH:26])=[O:25])[N:3]=[N:2]3)=[CH:20][CH:19]=2)=[O:9])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 238498Ethyl 3-oxohexanoateHCID 2723922Sodium ethoxideHCID 866298004-azido-N-(2-piperidin-1-ylethyl)benzamide

Product 1

HCID 68513562HCID 68513562, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Azido-N-(2-piperidin-1-ylethyl)benzamide obtained in Example 62a) and ethyl 3-oxohexanoate (1.08 ml, 6.44 mmol, 1.25 eq.) were dissolved in ethanol (20 ml), sodium ethoxide (487 mg, 6.44 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min, and then at 60° C. for 13 hr. Water (40 ml) was added to the reaction mixture, ethanol was evaporated, and the residue was washed twice with ethyl acetate-hexane (2:1, 50 ml). The aqueous layer was neutralized (pH 6-7) with 6N hydrochloric acid and concentrated. The residue was dissolved in isobutanol, THF and ethyl acetate, dried over anhydrous sodium sulfate and concentrated, and ethyl acetate and THF were added to the residue. The precipitate was collected by filtration, washed with ethyl acetate and dried to give the title compound as a pale-brown powder (purity 90%, 2.05 g, 4.78 mmol, 92.9%).

Workup

  1. waitat 60° C. for 13 hr
  2. customwas evaporated
  3. washthe residue was washed twice with ethyl acetate-hexane (2:1, 50 ml)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in isobutanol
  6. dry with materialTHF and ethyl acetate, dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. additionethyl acetate and THF were added to the residue
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with ethyl acetate
  11. customdried

Sources & evidence

ORD record
ord-d38b9edfaa1d451a813432c4d8d294ae
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

Loading…