Ammonia → HCID 67915906, compound

HRID 1029929Notes

Reaction equation

HRID 1029929 reaction equation
[NH3:1].C(O[C:5](=[N+:13]1[CH2:21][CH:20]2[CH:15]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17][CH2:18][C:19]2=[O:22])[CH2:14]1)[CH2:6][C:7]1[CH2:12][CH:11]=[CH:10][CH2:9][CH:8]=1)C>C(O)C.ClCCl>[C:7]1([CH2:6][C:5]([N:13]2[CH2:21][CH:20]3[CH:15]([C:16]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:17][CH2:18][C:19]3=[O:22])[CH2:14]2)=[NH:1])[CH2:12][CH:11]=[CH:10][CH2:9][CH:8]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86745650HCID 86745650, compound

Product 1

HCID 67915906HCID 67915906, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

A 5.4N solution (0.7 cc) of ammonia in ethanol is added to a stirred suspension of (3aRS,7aRS)-2-[1-ethoxy-2-(cyclohexa-1,4-dien-1-yl)-ethylidene]-4-oxo-7,7-diphenyl-perhydroisoindolium tetrafluoborate (2 g) in anhydrous dichloromethane (30 cc), which is cooled to -15° C. After the temperature has returned to ambient temperature, the reaction mixture is stirred for 20 hours and then washed with a 20% aqueous potassium carbonate solution (2×35 cc). The organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from acetonitrile (5 cc). The crystals obtained are drained, washed with acetonitrile and dried. (3aRS,7aRS)-2-[-2-(cyclohexa-1,4-dien-1-yl)-1-iminoethyl]-7,7-diphenyl-4-perhydroisoindolone (0.6 g) is obtained in the form of white crystals. m.p.=190° C.

Workup

  1. customhas returned to ambient temperature
  2. washwashed with a 20% aqueous potassium carbonate solution (2×35 cc)
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is crystallized from acetonitrile (5 cc)
  6. customThe crystals obtained
  7. washwashed with acetonitrile
  8. customdried

Sources & evidence

ORD record
ord-16f0a603445b42a189ce84e6b211da15
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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