4-(3,6-dihydro-2H-pyran-4-yl)-N-methylaniline → N-methyl-4-(oxan-4-yl)aniline

HRID 594812Notes

Reaction equation

HRID 594812 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:14]=[CH:13][C:10]([NH:11][CH3:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[CH3:12][NH:11][C:10]1[CH:9]=[CH:8][C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 1185975924-(3,6-dihydro-2H-pyran-4-yl)-N-methylaniline

Product 1

HCID 89073829N-methyl-4-(oxan-4-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 4-(3,6-dihydro-2H-pyran-4-yl)-N-methylaniline (200 mg, 1.05 mmol) in EtOAc (20 mL) under N2 was added 10% Pd/C (50 mg) at r.t. The reaction was stirred overnight under 1 atm H2. The reaction was filtered through Celite and concentrated to give 180 mg (89%) as a yellow solid. [M+H] Calc'd for C12H15NO, 190. Found, 190.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. concentrationconcentrated
  3. customto give 180 mg (89%) as a yellow solid

Sources & evidence

ORD record
ord-20cc0b958b8f4ac6b329e601a0266c0f
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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