3,5-Bis(trifluoromethyl)phenyl isocyanate → HCID 10098315, compound

HRID 907549Notes

Reaction equation

HRID 907549 reaction equation
Cl.Cl.[N:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:5][CH:4]=1.[F:23][C:24]([F:39])([F:38])[C:25]1[CH:26]=[C:27]([N:35]=[C:36]=[O:37])[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1>C(Cl)Cl>[F:23][C:24]([F:38])([F:39])[C:25]1[CH:26]=[C:27]([NH:35][C:36]([N:20]2[CH2:21][CH2:22][N:17]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][CH2:9][C:6]3[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=3)[CH2:18][CH2:19]2)=[O:37])[CH:28]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:30]=1

Participants

4

Reactant 2

HCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanateHCID 67387967HCID 67387967, compound

Product 1

HCID 10098315HCID 10098315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[2-(Pyridin-4-ylmethoxy)-phenyl]-piperazine dihydrochloride (0.3 mmol, 100 mg), DCM (5 ml), TEA (1 mmol, 139 ul), and 3,5-bis(trifluoromethyl)phenyl isocyanate (0.6 mmol, 104 ul) was stirred at room temperature overnight. The mixture was concentrated in vacuo and purified on silica column using 80% EtOAc/hexanes to give N-[3,5-bis(trifluoromethyl)phenyl]-4-{2-[(pyridin-4-ylmethyl)oxy]phenyl}piperazine-1-carboxamide. 1H NMR (CDCl3) 8.599-8.586 (d, 2H), 7.855 (s, 2H), 7.559-7.452 (d, 2H), 7.390-7.377 (d, 2H), 7.021-6.888 (m, 4H), 5.146 (s, 2H), 3.728-3.704 (m, 4H), 3.149-3.125 (m, 4H) ppm.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified on silica column

Sources & evidence

ORD record
ord-220ce9ddb7ad47758f7a3a26c0e7e0a5
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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