Benzaldehyde → HCID 14257727, compound

HRID 326447Notes

Reaction equation

HRID 326447 reaction equation
[C:1]([O-])(=O)[CH3:2].[NH4+:5].[CH3:6][OH:7].[Se:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C.CCOCC>[C:16]1([CH:15]2[NH:5][CH:11]([C:1]3[CH:2]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:10]3[C:6](=[O:7])[CH:12]2[CH2:13][Se:8][CH2:9]3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 887MethanolHCID 517165Ammonium AcetateHCID 13495457HCID 13495457, compound

Product 1

HCID 14257727HCID 14257727, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

A jacketed flask was charged with a solution of dry ammonium acetate (2.31 g, 30.0 mmol) in absolute ethanol (30 mL) which was warmed to 65° C. by boiling methanol in the jacket. A solution of 4-selenanone (2.45 g, 15.0 mmol) and benzaldehyde (3.18 g, 30.0 mmol) in absolute ethanol (15 mL) was added in one portion. The resulting solution was stirred under nitrogen at 65° C. for 45 minutes. After cooling the reaction mixture to about 30°-40° C., ether (15 mL) was added and stirring was continued for 10 minutes. Cooling (5° C.) overnight resulted in the formation of a yellow solid which was filtered and recrystallized (ethanol) to give 0.89 g (17%) of 6,8-diphenyl-3-selena-7-azabicyclo[3.3.1]nonan-9-one as white needles: mp 207.0°-208.5° C. (dec); IR (KBr) cm-1 3320 (N-H), 1730 (C=O); 1N NMR (DCCl3) δ1.77 [br s, 1H, H(7)], 2.84 [br d, 4H, H(2,4), J=8 Hz], 3.59 [m, 2H, H(1,5)], 5.04 [m, 2H, H(6,8)], 7.20-7.50 [m, 10H, ArH]; 13C NMR (DCCl3) ppm 92.2 [C(2,4)], 54.0 [C(1,5)], 64.2 [C(6,8)], 144.4 [C(1'), 127.0 [C(3',5') or C(2',6')], 127.9 [C(4')], 128.7 [C(2',6') or C(3',5)] 207.2 [C(9)]; 15N NMR (DCCl3) ppm 63.28 [N(7)]; 77Se NMR (DCCl3) ppm 25.38 [Se(3)]. Analysis calculated for C19H19NOSe: C, 64.04; H, 5.38; N, 3.93; Se, 22.17. Found: C, 63.86; H, 5.45; H, 3.81; Se, 21.90. ##STR29##

Workup

  1. temperatureAfter cooling the reaction mixture to about 30°-40° C.
  2. stirringstirring
  3. waitwas continued for 10 minutes
  4. temperatureCooling (5° C.) overnight
  5. customresulted in the formation of a yellow solid which
  6. filtrationwas filtered
  7. customrecrystallized (ethanol)

Sources & evidence

ORD record
ord-2b7b443d01894808bc62ed99ef5c0173
Source dataset
uspto-grants-1993_12
Patent number
US05268481

Reaction notes

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