Triethylamine → HCID 67915871, compound

HRID 1029956Notes

Reaction equation

HRID 1029956 reaction equation
Br.[C:2]1([CH2:8][C:9](=[NH:13])OCC)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[C:22]1([C:28]2([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:36]3[CH:32]([CH2:33][NH:34][CH2:35]3)[C:31](=[O:37])[CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[NH:13]=[C:9]([N:34]1[CH2:33][CH:32]2[CH:36]([C:28]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:29][CH2:30][C:31]2=[O:37])[CH2:35]1)[CH2:8][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 19899922HCID 19899922, compoundHCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

Product 1

HCID 67915871HCID 67915871, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Ethyl phenylacetimidate hydrobromide (1.2 g) and triethylamine (1.4 cc) are added to a stirred suspension of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (1.6 g) in 1,2-dichloroethane (40 cc). Stirring of the reaction mixture is continued for 20 hours at ambient temperature and then for 6 hours under reflux. After the temperature has returned to ambient temperature, the reaction mixture is treated with a saturated aqueous solution (50 cc) of potassium carbonate; the organic phase is dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from acetonitrile (20 cc). The crystals obtained are drained and dried. (3aRS,7aRS)-2-(α-iminophenethyl)-7,7-diphenyl-4-perhydroisoindolone (0.9 g) melting at 195° C. is obtained.

Workup

  1. temperaturefor 6 hours under reflux
  2. customhas returned to ambient temperature
  3. dry with materialthe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is crystallized from acetonitrile (20 cc)
  7. customThe crystals obtained
  8. customdried

Sources & evidence

ORD record
ord-8a3b766dc45a46d6ba93e3c6e05f6ca2
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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