Potassium Carbonate → HCID 54361557, compound

HRID 1196236Notes

Reaction equation

HRID 1196236 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]=[CH:11][C:10](=[O:13])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[CH2:25][N:26]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:27][Si](C)(C)C)CCC.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O.ClCCl>[CH2:32]([N:26]1[CH2:27][CH:9]2[CH:8]([C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:12]=[CH:11][C:10]2=[O:13])[CH2:25]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2968354,4-Diphenyl-2,5-cyclohexadien-1-oneHCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamine2×

Product 1

HCID 54361557HCID 54361557, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 drops) is added to a solution of 4,4-diphenyl-2,5-cyclohexadien-1-one (7.7 g) and N-butoxymethyl-N-(trimethylsilylmethyl)benzylamine (11 cc) in dry dichloromethane (80 cc), and the reaction mixture is heated to reflux for 1 hour and a half. A further portion (5 cc) of N-butoxymethyl-N-(trimethylsilylmethyl)benzylamine is added as well as trifluoroacetic acid (2 drops), and the reaction mixture is heated for 1 hour and a half. The reaction mixture is heated with potassium carbonate (3 g), filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in isopropyl ether (15 cc). The crystals obtained are drained, washed with isopropyl ether (2×5 cc) and dried; (3aRS,7aRS)-2-benzyl-7,7-diphenyl-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-one (4.4 g), m.p. 132° C., is obtained.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 1 hour
  3. temperaturethe reaction mixture is heated for 1 hour
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is crystallized in isopropyl ether (15 cc)
  7. customThe crystals obtained
  8. washwashed with isopropyl ether (2×5 cc)
  9. customdried

Sources & evidence

ORD record
ord-f1fd23f0dc714c578e1dac47642f2b51
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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