N,N-dimethyl-N-((2Z)-3-{3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridin-2-yl}prop-2-enyl)amine → 2-({2-[3-(Dimethylamino)propyl]pyridin-3-yl}oxy)ethanol

HRID 1765090Notes

Reaction equation

HRID 1765090 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3]/[CH:4]=[CH:5]\[C:6]1[C:11]([O:12][CH2:13][CH2:14][O:15]C2CCCCO2)=[CH:10][CH:9]=[CH:8][N:7]=1>CO.[Pd]>[CH3:22][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 1

HCID 69498118N,N-dimethyl-N-((2Z)-3-{3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridin-2-yl}prop-2-enyl)amine

Product 1

HCID 211066632-({2-[3-(Dimethylamino)propyl]pyridin-3-yl}oxy)ethanolYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of the cis and trans isomers N,N-dimethyl-N-((2E and 2Z)-3-{3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridin-2-yl}prop-2-enyl)amine (from Example 20, Step 2; 3.1 g, 10.1 mmol) in MeOH (50 mL) was added 10% Pd/C (0.30 g) and the mixture was hydrogenated in a Parr apparatus at room temperature at 70 psi H2 overnight. The solvent from the filtered solution was removed under reduced pressure and the tetrahydropyranyl protecting group was removed using the procedure described in Example 19, Step 4, to yield 1.29 g (57%) of the title compound as a brown oil. HRMS m/z calcd for C12H20N2O2 (M)+ 224.1525. found 224.1521.

Workup

  1. customwas hydrogenated in a Parr apparatus at room temperature at 70 psi H2 overnight
  2. customThe solvent from the filtered solution was removed under reduced pressure
  3. customthe tetrahydropyranyl protecting group was removed

Sources & evidence

ORD record
ord-4fe930b3b4eb49d09996b19d34d05458
Source dataset
uspto-grants-2007_06
Patent number
US07226925B2

Reaction notes

Loading…