Aluminium lithium hydride → 4-(1-Methylpiperidin-4-yl)-3-(trifluoromethyl)aniline

HRID 2200122Notes

Reaction equation

HRID 2200122 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20](OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[C:10]([C:27]([F:30])([F:29])[F:28])[CH:9]=1>C1COCC1>[CH3:20][N:17]1[CH2:16][CH2:15][CH:14]([C:11]2[CH:12]=[CH:13][C:8]([NH2:7])=[CH:9][C:10]=2[C:27]([F:28])([F:29])[F:30])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90028532Tert-butyl 4-(4-amino-2-(trifluoromethyl)phenyl)piperidine-1-carboxylate

Product 1

HCID 893060394-(1-Methylpiperidin-4-yl)-3-(trifluoromethyl)anilineYield 61.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add LiAlH4 (66.5 mg, 1.75 mmol) at 0° C. to the mixture of tert-butyl 4-(4-amino-2-(trifluoromethyl)phenyl)piperidine-1-carboxylat (151 mg, 0.438 mmol) in THF (3 mL), stir the reaction mixture overnight at room temperature. Quench the reaction with 15% sodium hydroxide solution, filter and concentrate the filtrate under reduced pressure. Purify the residue by flash chromatography (silica gel, DCM:MeOH=15:1) to afford the desired product (70 mg, 56%). MS: (M+1): 259.1.

Workup

  1. customQuench
  2. customthe reaction with 15% sodium hydroxide solution
  3. filtrationfilter
  4. concentrationconcentrate the filtrate under reduced pressure
  5. customPurify the residue by flash chromatography (silica gel, DCM:MeOH=15:1)

Sources & evidence

ORD record
ord-ec34673e743a4109a1b45d2f6a3107a8
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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