Trifluoroacetic acid → 3-Isopropylidene-1-(4-methoxy-benzyl)-piperidine

HRID 131046Notes

Reaction equation

HRID 131046 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14](O)([CH3:16])[CH3:15])[CH2:9]2)=[CH:5][CH:4]=1.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>>[C:14](=[C:10]1[CH2:11][CH2:12][CH2:13][N:8]([CH2:7][C:6]2[CH:18]=[CH:19][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:9]1)([CH3:16])[CH3:15]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 597302902-{1-(4-Methoxy-benzyl)-piperidin-3-yl]-propan-2-ol

Product 1

HCID 597300293-Isopropylidene-1-(4-methoxy-benzyl)-piperidineYield 76.2%

Procedure

Combine 2-{1-(4-Methoxy-benzyl)-piperidin-3-yl]-propan-2-ol (0.564 g, 2.14 mmol) and 1:1 Et3SiH:TFA (8 mL) at room temperature. Reflux the reaction for 72 hours under a Nitrogen atmosphere and then concentrate under reduced pressure and flash chromatograph using 3% 1N NH3-MeOH in CH2Cl2 to give 400.0 mg (76% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 1.5-1.6 (8H, d), 2.2 (2H, t), 2.5 (2H, br s), 3.0 (2H, br s), 3.5 (2H, br s), 3.8 (3H, s), 6.8 (2H, d), 7.2 (2H, d); MS m/z 246

Workup

  1. customat room temperature
  2. temperatureReflux
  3. customthe reaction for 72 hours under a Nitrogen atmosphere
  4. concentrationconcentrate under reduced pressure and flash chromatograph

Sources & evidence

ORD record
ord-937769ea0c124165be4ea4429724c74f
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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