Azacyclonol → HCID 21272257, compound

HRID 1193689Notes

Reaction equation

HRID 1193689 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([C:24]1[CH:34]=[CH:33][C:27]([O:28][CH2:29][CH2:30][CH2:31]Cl)=[C:26]([O:35][CH3:36])[CH:25]=1)(=[O:23])[CH3:22].[C:37](=[O:40])([OH:39])[O-].[Na+]>CN(C)C=O>[C:7]([OH:8])(=[O:23])[C:37]([OH:39])=[O:40].[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:8])[CH:9]2[CH2:14][CH2:13][N:12]([CH2:31][CH2:30][CH2:29][O:28][C:27]3[CH:33]=[CH:34][C:24]([C:21](=[O:23])[CH3:22])=[CH:25][C:26]=3[O:35][CH3:36])[CH2:11][CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 15723AzacyclonolHCID 516892Sodium BicarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenone

Product 1

HCID 21272257HCID 21272257, compoundYield 115.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5.2 g (0.0194 mole) of α,α-diphenyl-4-piperidinemethanol, 4.7 g (0.0194 mole) of 3-(p-acetyl-o-methoxyphenoxy)propyl chloride and 1.6 g (0.0194 mole) of sodium bicarbonate in 60 ml of dimethylformamide was stirred at 100° C. for 3 hrs. After cooling, the reaction mixture was filtered and the dimethylformamide was removed under reduced pressure. The residual oil weighed 8.3 g (90%). Some of the product crystallized upon trituration in anhydrous ether and was collected by filtration. The filtrate was evaporated to dryness and the residue was dissolved in hot benzene-isooctane. Upon cooling, the crystalline product was obtained. A total yield of 6.3 g of solid product was obtained. The solid free base was converted to the oxalate salt. Recrystallization from isobutyl methyl ketone gave the off-white solid melting at 174°-176° C. (See Ex. 15, U.S. Pat. No. 3,956,296).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customthe dimethylformamide was removed under reduced pressure
  4. customSome of the product crystallized upon trituration in anhydrous ether
  5. filtrationwas collected by filtration
  6. customThe filtrate was evaporated to dryness
  7. dissolutionthe residue was dissolved in hot benzene-isooctane
  8. temperatureUpon cooling
  9. customthe crystalline product was obtained

Sources & evidence

ORD record
ord-e69e14ed8ad24cc28b9950c94534af0c
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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