3-{3-[(4-Methylpiperidin-1-yl)methyl]phenoxy}propan-1-amine → HCID 13364672, compound

HRID 1981358Notes

Reaction equation

HRID 1981358 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=2)[O:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH2:4][CH2:3]1.Cl.[Cl-].[C:22](O)(=[O:30])[C:23]1[CH:28]=[CH:27][CH:26]=[N+:25]([O-:29])[CH:24]=1>N1C=CC=CC=1>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=2)[O:12][CH2:13][CH2:14][CH2:15][NH:16][C:22]([C:23]2[CH:24]=[N+:25]([O-:29])[CH:26]=[CH:27][CH:28]=2)=[O:30])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 133646653-{3-[(4-Methylpiperidin-1-yl)methyl]phenoxy}propan-1-amineHCID 86740065HCID 86740065, compound

Product 1

HCID 13364672HCID 13364672, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 0.023 mol of 3-[3-(4-methylpiperidinomethyl)phenoxy]propylamine and 30 ml of pyridine, stirred at 0° C., 0.047 mol of nicotinic acid 1-oxide chloride hydrochloride is added, portionwise; then the mixture is stirred for 1 hour at room temperature and the solvent is evaporated under reduced pressure. The residue is taken up with N hydrochloric acid and the salts thus obtained are eliminated by filtration, then the mixture is extracted 3 times with 100 ml of ethyl acetate and sodium hydroxide is added thereto to basic pH. The mixture is extracted with ethyl acetate containing 10% ethanol, the organic phase is dried over anhydrous sodium sulfate and the solvent is evaporated under reduced pressure. An oil which crystallizes slowly is obtained. The product is triturated in diethyl ether and filtered to give 4.5 g of crude product which is chromatographed on silica in a mixture methanol: chloroforme 15:35 and crystallized from ethyl acetate. Thus 2.7 g of N-[3-[3-(4-methylpiperidinomethyl)phenoxy] propyl]-3-pyridinecarboxamide 1-oxide are obtained, SR 58037, m.p. 109°-111° C.; yield: 35% of the theoretical value.

Workup

  1. stirringthen the mixture is stirred for 1 hour at room temperature
  2. customthe solvent is evaporated under reduced pressure
  3. customthe salts thus obtained
  4. filtrationare eliminated by filtration
  5. extractionthe mixture is extracted 3 times with 100 ml of ethyl acetate and sodium hydroxide
  6. additionis added
  7. extractionThe mixture is extracted with ethyl acetate containing 10% ethanol
  8. dry with materialthe organic phase is dried over anhydrous sodium sulfate
  9. customthe solvent is evaporated under reduced pressure
  10. customAn oil which crystallizes slowly
  11. customis obtained
  12. customThe product is triturated in diethyl ether
  13. filtrationfiltered
  14. customto give 4.5 g of crude product which
  15. customis chromatographed on silica in a mixture methanol: chloroforme 15:35
  16. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1fa5476e19fb4125ba494d6fc87b1395
Source dataset
uspto-grants-1985_04
Patent number
US04514408

Reaction notes

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