Triethylamine → HCID 72309466, compound

HRID 2400562Notes

Reaction equation

HRID 2400562 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([O:7][CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:25][OH:26].C(N(CC)CC)C>C(O)C>[OH:26][N:25]=[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH2:14]2)=[CH:22][CH:23]=1)[NH2:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 10639134HCID 10639134, compound

Product 1

HCID 72309466HCID 72309466, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 4-[(4-cyanophenoxy)methyl]piperidine-1-carboxylate (Step 1, 1.47 g, 4.22 mmol, purity 91%), hydroxylamine hydrochloride (646 mg, 9.30 mmol) and triethylamine (1.30 mL, 9.30 mmol) in ethanol (24 mL) was stirred and heated at reflux for 1 h. After being cooled to rt, the reaction mixture was evaporated to dryness. The resulting material was treated with ethyl acetate, and the solid was filtered off. The ethyl acetate solution was washed with water and saturated sodium chloride solution, dried with anhydrous magnesium sulfate and filtered. After evaporation of the solvent, the crude product was stirred in tert-butyl methyl ether. The solid was filtered off and dried in vacuo to give the title compound (1.16 g, 78%): 1H NMR (400 MHz, CDCl3) δ 7.53 (d, 2H), 6.89 (d, 2H), 4.82 (s, 2H), 4.22-4.08 (broad m, 2H), 3.81 (d, 2H), 2.81-2.66 (m, 2H), 2.02-1.90 (m, 1H), 1.85-1.78 (d, 2H), 1.46 (s, 9H), 1.35-1.18 (m, 2H); ES-MS m/z 350, HPLC RT (Method D) 1.56 min.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. customthe reaction mixture was evaporated to dryness
  4. additionThe resulting material was treated with ethyl acetate
  5. filtrationthe solid was filtered off
  6. washThe ethyl acetate solution was washed with water and saturated sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customAfter evaporation of the solvent
  10. filtrationThe solid was filtered off
  11. customdried in vacuo

Sources & evidence

ORD record
ord-4f4b4cd54f044b08bce7ff0759795b89
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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