Triethylamine → N-[3,5-bis(trifluoromethyl)phenyl]-4-{2-[(pyridin-4-yloxy)methyl]phenyl}-piperazine-1-carboxamide

HRID 907580Notes

Reaction equation

HRID 907580 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:28][C:29]([F:44])([F:43])[C:30]1[CH:31]=[C:32]([N:40]=[C:41]=[O:42])[CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1>ClCCl>[F:28][C:29]([F:43])([F:44])[C:30]1[CH:31]=[C:32]([NH:40][C:41]([N:18]2[CH2:19][CH2:20][N:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][O:7][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH2:16][CH2:17]2)=[O:42])[CH:33]=[C:34]([C:36]([F:39])([F:37])[F:38])[CH:35]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanateHCID 673880841-[2-(Pyridin-4-yloxymethyl)phenyl]piperazine

Product 1

HCID 86616582N-[3,5-bis(trifluoromethyl)phenyl]-4-{2-[(pyridin-4-yloxy)methyl]phenyl}-piperazine-1-carboxamideYield 10.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The impure 1-[2-(Pyridin-4-yloxymethyl)phenyl]piperazine (˜50 mg) was dissolved in 5 mL of dichloromethane along with triethylamine (50 μL, 0.36 mmol). 3,5-Bis(trifluoromethyl)phenyl isocyanate (50 μL, 0.29 mmol) was added and the reaction was stirred at room temperature overnight. The solvent was removed under vacuum and the residue was dissolved in 2 mL methanol. The reaction mixture was purified by reverse phase HPLC to give 10 mg of product as a white solid. 1H NMR (DMSO-d6) δ 10.58 (s, 1H), 8.28 (d, 2H), 8.17 (s, 2H), 7.73 (s, 1H), 7.49 (d, 1H), 7.38 (t, 1H), 7.18-7.25 (m, 4H), 5.39 (s, 2H), 3.80-3.85 (m, 4H) 3.00-3.04 (m, 4H).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in 2 mL methanol
  3. customThe reaction mixture was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-e8fa43cfaf9b4152af69fae89094cc25
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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