HCID 90405565, compound → HCID 86271948, compound

HRID 2277079Notes

Reaction equation

HRID 2277079 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[CH:11]=[C:12](/[CH:16]=[CH:17]/[CH2:18][NH2:19])[CH:13]=[CH:14][CH:15]=2)[CH2:4][CH2:3]1>CCO.[Pd]>[O:2]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH2:16][CH2:17][CH2:18][NH2:19])[CH:13]=[CH:14][CH:15]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 90405565HCID 90405565, compound

Product 1

HCID 86271948HCID 86271948, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogenation of Example 31 ((E)-3-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)prop-2-en-1-amine hydrochloride) at 1 atm H2 pressure using Pd/C (10% wt, 0.020 g) catalyst in EtOH (absolute, degassed, 20 mL) for 1.5 hrs gave after filtration through Celite and concentration of the filtrate under reduced pressure Example 32 hydrochloride as a white solid. Yield (0.150 g, 73%); 1H NMR (400 MHz, DMSO-d6) δ 7.98 (br. s, 3H), 7.18 (t, J=7.83 Hz, 1H), 6.72-6.80 (m, 3H), 3.750-3.90 (m, 4H), 3.26-3.36 (m, 2H), 2.72 (t, J=7.24 Hz, 2H), 2.59 (t, J=7.43 Hz, 1H), 1.96 (m, 1H), 1.78-1.88 (m, 2H), 1.61-1.69 (m, 2H), 1.24-1.36 (m, 2H); MS: m/z 250.2 [M+H]+.

Workup

  1. filtrationafter filtration through Celite and concentration of the filtrate under reduced pressure Example 32 hydrochloride as a white solid
  2. customYield (0.150 g, 73%)

Sources & evidence

ORD record
ord-05fff5b2f7514d84a120a2c495a9d152
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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