Hydrochloric Acid → (3,5-Bis-trifluoromethyl-benzyl)-methyl-(3-o-tolyl-pyridin-4-ylmethyl)-amine

HRID 1975958Notes

Reaction equation

[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:6][N:7]([CH3:23])[C:8](=O)[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21].Cl.[OH-].[Na+].C(OCC)(=O)C>O1CCCC1.CCOCC>[F:29][C:27]([F:28])([F:30])[C:25]1[CH:24]=[C:5]([CH:4]=[C:3]([C:2]([F:32])([F:31])[F:1])[CH:26]=1)[CH2:6][N:7]([CH3:23])[CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 0.12 g (0.265 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-3-o-tolyl-isonicotinamide in 3 ml tetrahydrofuran 1.6 ml of a 1M solution of BH3 in tetrahydrofuran was added and the reaction mixture stirred for 16 h at 60° C. After addition of 2 ml 3M HCl in ether the reaction mixture was stirred for 3 h at 60° C. The solution was cooled to room temperature and 5 ml 3N sodium hydroxide solution and 10 ml ethyl acetate were added. Stirring was continued for ½ h, the phases separated and the aqueous phase extracted twice with 15 ml ethyl acatate. The combined organic layers were washed with brine, dried (magnesium sulfate) and evaporated. Chromatography of the residue afforded 0.30 g (25%) of the title compound as a pale yellow oil.

Workup

stirringwas stirred for 3 h at 60° C
temperatureThe solution was cooled to room temperature
stirringStirring
waitwas continued for ½ h
customthe phases separated
extractionthe aqueous phase extracted twice with 15 ml ethyl acatate
washThe combined organic layers were washed with brine
dry with materialdried (magnesium sulfate)
customevaporated

Sources & evidence

ORD record: ord-f5e4b20a80f54e3b96babfc23aa4bd9c
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06225316B1

Reaction notes

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