Acetic Acid → HCID 14257723, compound

HRID 868413Notes

Reaction equation

HRID 868413 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]([OH:13])(=O)[CH3:11].[CH2:14]=O.[Se:16]1[CH2:21]C[C:19](=O)[CH2:18][CH2:17]1.[OH-].[Na+]>CO.O>[CH2:1]([N:9]1[CH2:19][CH:18]2[C:10](=[O:13])[CH:11]([CH2:21][Se:16][CH2:17]2)[CH2:14]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 5

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

Product 1

HCID 14257723HCID 14257723, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution 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 evaported (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 extracted 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 δ2.62-283 [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)], 125.9 [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. extractionwas then extracted with ether (5×40 mL)
  5. washThe combined extracts were washed with saturated brine
  6. dry with materialdried (K2CO3)
  7. customEvaporation (aspirator)
  8. customgave a brown residue which
  9. customEvaporation of the Skelly B (150 mL)
  10. customEvaporation of the Skelly B
  11. customgave a solid which
  12. customwas recrystallized (ethanol)

Sources & evidence

ORD record
ord-f52f649573694b33bdacd73c7b15a839
Source dataset
uspto-grants-1988_10
Patent number
US04778892

Reaction notes

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