Water → 1-Benzyl-4-trifluoromethyl-1,2,3,6-tetrahydro-pyridine

HRID 734769Notes

Reaction equation

[BH4-].[Na+].[Cl-].[CH2:4]([N+:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>CCO>[CH2:4]([N:11]1[CH2:12][CH:13]=[C:14]([C:17]([F:20])([F:18])[F:19])[CH2:15][CH2:16]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3.00 g (79.36 mmol) of sodium borohydride was added batchwise to a solution of 14.48 g (52.91 mmol) of 1-benzyl-4-trifluoromethylpyridinium chloride in 100 mL of EtOH with strong cooling at 0° C., then the cooling was stopped and the reaction mixture was stirred for 1.5 hours at 14° C. While cooling, 50 mL of water and then 50 mL of EtOH were added within 30 minutes. The reaction mixture was stirred for another 30 minutes, the resulting suspension was filtered and the filtrate was evaporated down in vacuo. Yield: 11.72 g (92% of theoretical); C13H14F3N (M=241.252); calc.: molpeak (M+H)+: 242; found: molpeak (M+H)+: 242; HPLC-MS: 3.60 minutes (method B).

Workup

temperatureWhile cooling
stirringThe reaction mixture was stirred for another 30 minutes
filtrationthe resulting suspension was filtered
customthe filtrate was evaporated down in vacuo
custom3.60 minutes (method B)

Sources & evidence

ORD record: ord-b14a544d28454d6c99a6a0df623a34b1
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592358B2

Reaction notes

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