Acetic Acid → HCID 14257723, compound

HRID 2249310Notes

Reaction equation

HRID 2249310 reaction equation
[Na].[CH2:2]([NH2:10])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([OH:14])(=O)[CH3:12].[CH2:15]=O.[Se:17]1[CH2:22]C[C:20](=O)[CH2:19][CH2:18]1.[OH-].[Na+]>CO>[CH2:2]([N:10]1[CH2:20][CH:19]2[C:11](=[O:14])[CH:12]([CH2:22][Se:17][CH2:18]2)[CH2:15]1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 712FormaldehydeHCID 1001PhenethylamineHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 13495457HCID 13495457, compound

Product 1

HCID 14257723HCID 14257723, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A sodium was made of phenethylamine (1.48 g, 12.3 mmol) and glacial acetic acid (0.85 g, 14.2 mmol) in methanol (60 mL). Paraformaldehyde (3.0 g, 100 mmol) was added and the resulting mixture was heated to reflux with magnetic stirring under an atmosphere of nitrogen. 4-Selenanone (2.00 g, 12.3 mmol) was added and boiling was continued for 5 hours resulting in an orange solution. Methanol was evaporated (aspirator) and the residual orange oil was mixed with water (200 mL). This aqueous mixture was made basic by addition of NaOH (2.0 g, 50 mmol) and was then extract with ether (5×40 mL). The combined extracts were washed with saturated brine and dried (K2CO3). Evaporation (aspirator) gave a brown residue which was digested in boiling Skelly B (150) mL). Evaporation of the Skelly B (150 mL). Evaporation of the Skelly B gave a solid which was recrystallized (ethanol) to give 0.82 g (22%) of 7-phenethyl-3 -selena-7-azabicyclo[3.3.1]nonan-9-one as a light tan solid: mp 91°-92° C.; IR (KBr) cm-1 1710 (C=O); 1H NMR (DCCl3 δ262-2.83 [m, 8H, H(2,4,1,5,10-ArCH2)], 3.02-3.20 [m, 6H, H(6,8,11-NCH2)], 7.16-7.38 [m, 5H, Ar-H]; 13C NMR (DCCl3) ppm 25.4 [5, C(2,4)], 33.7 [5, C(10-ArCH2)], 46.2 [d, C(1,5)], 58.3 [5, C(11-NCH2)], 59.1 [t, C(6,8)], 125.8 [s, C(4')], 128.1 [d, C(2',6') or C(3',5')], 128.4 [d, C(3',5') or C(2',6')], 139.7 [s, C(1')], 213.5 [s, C(9 )]; 15N NMR (DCCl3) ppm 35.44 [N(7)]; 77Se NMR (DCCl3) ppm 79.51 [Se(3)]. The compound was converted to the hydroperchlorate salt without further purification. ##STR21##

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux
  3. customresulting in an orange solution
  4. customMethanol was evaporated (aspirator)
  5. additionthe residual orange oil was mixed with water (200 mL)
  6. extractionwas then extract with ether (5×40 mL)
  7. washThe combined extracts were washed with saturated brine
  8. dry with materialdried (K2CO3)
  9. customEvaporation (aspirator)
  10. customgave a brown residue which
  11. customEvaporation of the Skelly B (150 mL)
  12. customEvaporation of the Skelly B
  13. customgave a solid which
  14. customwas recrystallized (ethanol)

Sources & evidence

ORD record
ord-303e8f4a6549467bba8f63d5a1236c06
Source dataset
uspto-grants-1991_08
Patent number
US05043445

Reaction notes

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