3-Chloro-4-(trifluoromethyl)aniline → HCID 11596912, compound

HRID 603164

Reaction equation

HRID 603164 reaction equation
[C:1](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:2].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[C:19]([Cl:27])[CH:18]=1.[CH3:28][N:29]1[CH2:34][CH2:33][CH2:32][CH:31]([CH2:35][N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:30]1>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:27][C:19]1[CH:18]=[C:17]([NH:16][C:1]([N:39]2[CH2:40][CH2:41][N:36]([CH2:35][CH:31]3[CH2:32][CH2:33][CH2:34][N:29]([CH3:28])[CH2:30]3)[CH2:37][CH2:38]2)=[O:2])[CH:22]=[CH:21][C:20]=1[C:23]([F:24])([F:25])[F:26]

Participants

6

Reactant 3

HCID 679623-Chloro-4-(trifluoromethyl)anilineHCID 90495Di-tert-butyl dicarbonateHCID 27369401-[(1-Methylpiperidin-3-yl)methyl]piperazine

Product 1

HCID 11596912HCID 11596912, compoundYield 6.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent3×

Procedure

To a solution of di-tert-butyl dicarbonate (114.6 mg) in chloroform (2 ml) was added 4-dimethylaminopyridine (6 mg). A solution of 4-amino-2-chlorobenzotrifluoride (98.1 mg) in chloroform (2 ml) was added and the reaction mixture stirred for 20 minutes at room temperature. A solution of 1-[(1-methylpiperidin-3-yl)methyl]piperazine (98.5 mg) in chloroform (2 ml) was added and the resulting solution was stirred at reflux for 18 hours. The reaction mixture was purified by column chromatography on silica gel (20 g) using a gradient of 100% dichloromethane through to 20% methanolic ammonia in dichloromethane to give the title compound (14 mg).

Workup

  1. stirringthe resulting solution was stirred
  2. temperatureat reflux for 18 hours
  3. customThe reaction mixture was purified by column chromatography on silica gel (20 g)

Sources & evidence

ORD record
ord-756c6bebf35b4f39a1dcfd943e37587b
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Linked notes

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