Sodium Bicarbonate → HCID 14407146, compound

HRID 1193688Notes

Reaction equation

HRID 1193688 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.[C:22]([C:25]1[CH:35]=[CH:34][C:28]([O:29][CH2:30][CH2:31][CH2:32]Cl)=[C:27]([O:36][CH3:37])[CH:26]=1)(=[O:24])[CH3:23].C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:9])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:10]2[CH2:15][CH2:14][N:13]([CH2:32][CH2:31][CH2:30][O:29][C:28]3[CH:34]=[CH:35][C:25]([C:22](=[O:24])[CH3:23])=[CH:26][C:27]=3[O:36][CH3:37])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 14698744HCID 14698744, compound

Product 1

HCID 14407146HCID 14407146, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.5 g (0.023 mole) of α-(p-fluorophenyl)-α-phenyl-4-piperidinemethanol, 5.5 g (0.023 mole) of 3-(p-acetyl-o-methoxyphenoxy)propyl chloride and 1.92 g (0.023 mole) of sodium bicarbonate in 80 ml of dimethylformamide was heated at 100°-110° C. for 2 hrs. The reaction mixture was cooled and filtered and the dimethylformamide was removed at reduced pressure. The residual oil was dissolved in chloroform and filtered. The chloroform was removed at reduced pressure. The solid residue which remained weighed 8.6 g (77%) and was recrystallized from ethanol to give 3.1 g of material melting at 147°-148° C. A sample was dried over refluxing toluene and submitted for analysis. (See Ex. 14, U.S. Pat. No. 3,956,296).

Workup

  1. temperaturewas heated at 100°-110° C. for 2 hrs
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customthe dimethylformamide was removed at reduced pressure
  5. dissolutionThe residual oil was dissolved in chloroform
  6. filtrationfiltered
  7. customThe chloroform was removed at reduced pressure
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-1f8e8be4affd449393cb30fe0503d5c8
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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