HCID 14500437, compound → HCID 14500417, compound

HRID 1762908Notes

Reaction equation

HRID 1762908 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:4]=1[O:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[OH:8]>CO.[Pt]=O>[ClH:1].[CH3:2][C:3]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:4]=1[O:5][CH2:6][CH:7]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][NH:10]1)[OH:8]

Participants

4

Reactant 1

HCID 14500437HCID 14500437, compound

Product 1

HCID 14500417HCID 14500417, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of α-[(2,6-dimethylphenoxy)methyl]pyridine-2-methanol hydrochloride (11.20 g, 0.04 mole) in 200 ml of methanol was hydrogenated at room temperature with 1.4 g of platinum oxide for 45 minutes. The solution was filtered and the methanol removed by rotary evaporator. Trituration with ethyl ether gave a white solid which was recrystallized from methanol-ethyl ether (and dried at 100° C. overnight) to give 7.81 g (67.5%) of white crystalline product, m.p. 178°-179° C. with decomposition.

Workup

  1. filtrationThe solution was filtered
  2. customthe methanol removed by rotary evaporator
  3. customTrituration with ethyl ether gave a white solid which
  4. customwas recrystallized from methanol-ethyl ether (and dried at 100° C. overnight)

Sources & evidence

ORD record
ord-9db4cd720c86496895eef4fbe95d78e1
Source dataset
uspto-grants-1989_05
Patent number
US04835164

Reaction notes

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