Isopropanol → HCID 178526270, compound

HRID 365108Notes

Reaction equation

HRID 365108 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:31]=[CH:32][CH:33]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:21]=[C:20]([O:22]CC3C=CC=CC=3)[CH:19]=[CH:18][N+:17]=2[O-:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C)C.C(O)(C)C.CC(C)=O>C(O)C.[Pd]>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:31]=[CH:32][CH:33]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][N+:17]=2[O-:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 22386392HCID 22386392, compoundHCID 178526272HCID 178526272, compound

Product 1

HCID 178526270HCID 178526270, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-[3-[3-(Piperidinomethyl)phenoxy]propylamino]-4-benzyloxypyridine-N-oxide (0.94 g) in ethanol (100 ml) was hydrogenated at 344 KPa (50 p.s.i), for 5 hours in the presence of 10% palladium on charcoal (0.1 g). The reaction mixture was filtered and the filtrate evaporated under reduced pressure to give an oil. Trituration under diethyl ether containing a little isopropanol gave as a buff solid 2-[3-[3-(piperidinomethyl)phenoxy]propylamino]-4-hydroxypyridine-N-oxide (0.59 g), m.p. 140°-142.5° C. (recrystallised from isopropanol-acetone).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. customto give an oil

Sources & evidence

ORD record
ord-d1bae3522b54481ea859e950a5a77e22
Source dataset
uspto-grants-1986_08
Patent number
US04608380

Reaction notes

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