Benzylamine → HCID 54143590, compound

HRID 981723Notes

Reaction equation

HRID 981723 reaction equation
[CH2:1]([C:4]12[CH2:10][CH:7]([CH:8]=[CH:9]1)[CH2:6][CH:5]2[C:11]([O:13]C)=O)[CH:2]=[CH2:3].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+]>C(Cl)Cl>[CH2:15]([NH:22][C:11]([CH:5]1[CH2:6][CH:7]2[CH2:10][C:4]1([CH2:1][CH:2]=[CH2:3])[CH:9]=[CH:8]2)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 25517Ammonium ChlorideHCID 20070593HCID 20070593, compound

Product 1

HCID 54143590HCID 54143590, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9.6 g of methyl allylbicyclo[2.2.1]hept-5-ene-2-carboxylate are mixed with 30 ml of benzylamine and 1 g of ammonium chloride, and the mixture is heated for 3 hours under reflux. After cooling, 100 ml of methylene chloride are added, and the reaction mixture is washed with 1N HCl, aqueous soda solution and saturated sodium chloride solution. The organic phase is dried and filtered, and the filtrate is concentrated, affording 3.8 g (73.4% of theory) of a red liquid resin. For the purpose of characterisation, a sample is distilled in a bomb tube. The distillate is a pale yellow oil; η25 =310 mPas.

Workup

  1. temperaturethe mixture is heated for 3 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. washthe reaction mixture is washed with 1N HCl, aqueous soda solution and saturated sodium chloride solution
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated
  8. customaffording 3.8 g (73.4% of theory) of a red liquid resin
  9. distillationFor the purpose of characterisation, a sample is distilled in a bomb tube

Sources & evidence

ORD record
ord-89ab1fbd7c09438896a93fb84402aabc
Source dataset
uspto-grants-1991_02
Patent number
US04992518

Reaction notes

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