4-Piperidinol, 1-methyl- → HCID 67521137, compound

HRID 1925399Notes

Reaction equation

HRID 1925399 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.CC(C)([O-])C.[K+].F[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=1[N+:26]([O-:28])=[O:27]>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][C:17]=2[N+:26]([O-:28])=[O:27])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 660484-Piperidinol, 1-methyl-HCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 67521137HCID 67521137, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-methylpiperidin-4-ol (2.99 mmol, 344.4 mg) was added to a suspension of potassium tert-butoxide in THF (5 mL) and stirred at RT for 30 minutes. 2-fluoro-5-trifluoromethyl nitrobenzene (2.39 mmol, 500 mg) was then added and the reaction mixture was stirred an additional 5 h at RT, at which time LC-MS showed complete conversion to the desired product. The reaction mixture was concentrated and the dark brown residue was taken up in methylene chloride (25 mL). This was washed with water (3×20 mL), dried over sodium sulfate, filtered and concentrated to give the crude product as a yellow oil. Crude material (>90% purity) was taken to the next step without further purification LC-MS: 305.1 (M+H)

Workup

  1. stirringthe reaction mixture was stirred an additional 5 h at RT, at which time LC-MS

Sources & evidence

ORD record
ord-0750aaa4bf5a4ecb9feca3fb79c29272
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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