Methanol → HCID 86738024, compound

HRID 1902672Notes

Reaction equation

HRID 1902672 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[C:7]1([N:13]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH:21]=[C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[CH2:19][CH2:18]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CO.[H][H]>[Pd].C(O)(=O)C>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[C:34]1([N:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:14][CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][CH:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=3)[CH2:21][CH2:22]2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 86738025HCID 86738025, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86738024HCID 86738024, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 7.7 g. (0.014 moles) of 3,6-dihydro-N,N-diphenyl-4-[3-(trifluoromethyl)phenoxy]-1(2H)-pyridinepropanamine ethanedioate (1:1) (preparation described in Example 16), 90 ml. of methanol, 10 ml. of acetic acid and 0.5 g. of 20% Pd/c is shaken under 50 psi. of hydrogen at room temperature for about 4 hours. The reaction mixture is then filtered, and the solvent is evaporated. The residue is initially recrystallized from aqueous isopropanol, then recrystallized from aqueous isopropanol, and again recrystallized from aqueous ethanol to give 5.0 g of N,N-diphenyl-4-[3-(trifluoromethyl)phenoxy]-1-piperidinepropanamine ethanedioate (1:1), mp. 189°-190.5° C.

Workup

  1. additionA mixture of 7.7 g
  2. filtrationThe reaction mixture is then filtered
  3. customthe solvent is evaporated
  4. customThe residue is initially recrystallized from aqueous isopropanol
  5. customrecrystallized from aqueous isopropanol
  6. customagain recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-0e337c7583bf4fa485ab48f5c190e261
Source dataset
uspto-grants-1982_12
Patent number
US04364954

Reaction notes

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