Benzylamine → HCID 15818604, compound

HRID 1720866Notes

Reaction equation

HRID 1720866 reaction equation
Cl[CH2:2][CH:3]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[CH:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[CH2:19]([NH:26][CH2:2][CH:3]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[CH:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 15818603HCID 15818603, compound

Product 1

HCID 15818604HCID 15818604, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-(2'-chloroethylidene)-5H dibenzo[a,d]cycloheptene (1.25 g, 5 mmol) in acetonitrile (30 ml) is added benzylamine (1.6 g, 15 mmol) and the mixture is refluxed for 4 hours under argon atmosphere. The solution is concentrated in vacuo, the residue is taken up in water, and the solution is basified with concentrated aqueous sodium bicarbonate. The water phase is extracted with ethyl acetate. The organic mixture is dried over magnesium sulfate, filtered and concentrated in vacuo. The residue (1.2 g) is dissolved in ether and a solution of oxalic acid (0.5 g) in tetrahydrofuran is added. The oxalate salt precipitates, and is recrystallized twice from ethanol, m.p. 209° C.

Workup

  1. temperaturethe mixture is refluxed for 4 hours under argon atmosphere
  2. concentrationThe solution is concentrated in vacuo
  3. extractionThe water phase is extracted with ethyl acetate
  4. dry with materialThe organic mixture is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue (1.2 g) is dissolved in ether
  8. additiona solution of oxalic acid (0.5 g) in tetrahydrofuran is added
  9. customThe oxalate salt precipitates
  10. customis recrystallized twice from ethanol, m.p. 209° C.

Sources & evidence

ORD record
ord-b50998a278ad48babf3aac753d03b4ce
Source dataset
uspto-grants-1996_04
Patent number
US05508280

Reaction notes

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