Oxalic Acid → 1-[4-[3-[4-[Bis(4-methoxyphenyl)hydroxymethyl]-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone oxalate

HRID 1709909Notes

Reaction equation

HRID 1709909 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].C1(C(C2C=CC=CC=2)=C2CCN(CCCOC3C=CC=CC=3)CC2)C=CC=CC=1.[CH3:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]([C:52]2[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][CH:53]=2)([CH:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[OH:45])=[CH:40][CH:39]=1.Cl[CH2:61][CH2:62][CH2:63][O:64][C:65]1[CH:70]=[CH:69][C:68]([C:71](=[O:73])[CH3:72])=[CH:67][C:66]=1[O:74][CH3:75].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].C(O)(=O)C(O)=O>C(O)CCC>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH3:59][O:58][C:55]1[CH:54]=[CH:53][C:52]([C:44]([C:41]2[CH:42]=[CH:43][C:38]([O:37][CH3:36])=[CH:39][CH:40]=2)([OH:45])[CH:46]2[CH2:51][CH2:50][N:49]([CH2:61][CH2:62][CH2:63][O:64][C:65]3[CH:70]=[CH:69][C:68]([C:71](=[O:73])[CH3:72])=[CH:67][C:66]=3[O:74][CH3:75])[CH2:48][CH2:47]2)=[CH:57][CH:56]=1

Participants

8

Reactant 6

HCID 971Oxalic AcidHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 14698742alpha,alpha-Bis(4-methoxyphenyl)-4-piperidinemethanolHCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

Product 1

HCID 230363121-[4-[3-[4-[Bis(4-methoxyphenyl)hydroxymethyl]-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone oxalate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

This compound was prepared according to the procedure used to synthesize the compound of Example 1. A mixture of 3.2 g (0.01 mole) of α,α-bis(4-methoxypenyl)-4-piperidinemethanol, 2.4 g (0.01 mole) of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone, 3.7 g (0.035 mole) of anhydrous sodium carbonate and 0.4 g of potassium iodide in 100 ml of 1-butanol gave a gum as residue. The gum was purified by columm chromatography on 100 g of Florisil®. Fractions eluted with 5-40% acetone in benzene were combined and concentrated under reduced pressure to give a brown glass as residue. The glass was converted to the oxalic acid salt. The solid was recrystallized from absolute ethanol yield 3.3 g (53%) of the title compound as a white solid, mp 139°-142° C. with decomposition.

Workup

  1. customThis compound was prepared
  2. customgave a gum as residue
  3. customThe gum was purified by columm chromatography on 100 g of Florisil®
  4. washFractions eluted with 5-40% acetone in benzene
  5. concentrationconcentrated under reduced pressure
  6. customto give a brown glass as residue
  7. customThe solid was recrystallized from absolute ethanol yield 3.3 g (53%) of the title compound as a white solid, mp 139°-142° C. with decomposition

Sources & evidence

ORD record
ord-c6b36e830901451c9996c5ae68c9899a
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

Loading…