Acetic Acid → HCID 14257725, compound

HRID 868414Notes

Reaction equation

HRID 868414 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). Evaporation 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(1,5)], 54.2 [OCH3 ], 57.8 [C(11-NCH2)], 58.2 [C(6,8)], 112.8 [C(3',5'), 128.5 [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. customEvaporation of the ether (aspirator)

Sources & evidence

ORD record
ord-2c0cf0343ee94afb8a9b7abca8b74d24
Source dataset
uspto-grants-1988_10
Patent number
US04778892

Reaction notes

Loading…