Acetic Acid → HCID 14257725, compound

HRID 2249311Notes

Reaction equation

HRID 2249311 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH2:9])=[CH:5][CH:4]=1.[C:12]([OH:15])(=O)[CH3:13].[CH2:16]=O.[Se:18]1[CH2:23]C[C:21](=O)[CH2:20][CH2:19]1.[OH-].[K+]>CO.O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][N:9]2[CH2:21][CH:20]3[C:12](=[O:15])[CH:13]([CH2:23][Se:18][CH2:19]3)[CH2:16]2)=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 4657O-MethyltyramineHCID 14797Potassium HydroxideHCID 13495457HCID 13495457, compound

Product 1

HCID 14257725HCID 14257725, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution was made of p-methoxyphenethylamine (0.93 g, 6.16 mmol) and glacial acetic acid (0.50 g, 8.33 mmol) in methanol (40 mL). Paraformaldehyde (1.50 g, 50.0 mmol) was added and the resulting mixture was heated to reflux under an atmosphere of nitrogen. 4-Selenanone 10 (1.00 g, 613 mmol) was added in one portion and boiling was continued for 4 hours. The methanol was evaporated (aspirator) from the resulting orange solution to give a very viscous red oil. This oil was dissolved in water (150 mL) and KOH (85%, 1.0 g, 15.2 mmol) was added to make the solution very basic. The resulting yellow suspension was extracted with ether (5×40 mL). The combined extracts were washed with water 930 mL) and dried (K2CO3). Evaporator of the ether (aspirator) gave 0.72 g (35%) 7-p-methoxyphenethyl-3-selena-7-azabicyclo[3.3.1]nonan-9-one as a light yellow oil: IR (neat) cm-1 1723 (C=O); 1H NMR (DCCl3) δ2.50-2.80 [m, 8H, H(1,5,2,4,10-ArCH2)], 2.96-3.14 [m, 6H, H(6,8,11, NCH2)], 3.71 [s, 3H, OCH3 ], 6.72-6.90 [m, 2H, H(3',5')], 7.00-7.16 [m, 2H, H(2',6')]; 13C NMR (DCCl3) ppm 24.6 [C(2,4)], 32.0 [C(10-ArCH2)], 45.4 [C(2',6')], 130.9 [C(1')], 156.9 [C(4')], 212.5 [C(9)]; 15N NMR (DCCl3) ppm 35.43 [N(7)]; 77Se NMR (DCCl3) [Se(3)] ppm 78.81. Without further purification the compound was converted to the hydroperchlorate salt. ##STR22##

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under an atmosphere of nitrogen
  3. customThe methanol was evaporated (aspirator) from the resulting orange solution
  4. customto give a very viscous red oil
  5. extractionThe resulting yellow suspension was extracted with ether (5×40 mL)
  6. washThe combined extracts were washed with water 930 mL) and
  7. dry with materialdried (K2CO3)
  8. customEvaporator of the ether (aspirator)

Sources & evidence

ORD record
ord-6f60f83ea071491e9591934f6afaf3d2
Source dataset
uspto-grants-1991_08
Patent number
US05043445

Reaction notes

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