Nomifensine → HCID 3029034, compound

HRID 485831Notes

Reaction equation

HRID 485831 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][N:9]([CH3:12])[CH2:8][CH:7]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C1C=CC=CC=1>[CH2:23]([O:22][C:20]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][N:9]([CH3:12])[CH2:8][CH:7]2[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:21])[CH3:24]

Participants

4

Reactant 2

HCID 4528NomifensineHCID 10928Ethyl chloroformate

Product 1

HCID 3029034HCID 3029034, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 5.5 g 0.023 mole of 8-amino-4-phenyl-2-methyl-1,2,3,4-tetrahydro-isoquinoline and 50 ml of anhydrous benzene a solution of 3.4 g (0.031 mole) of ethyl chloroformate and 30 ml of anhydrous benzene is added. The reaction mixture is heated to boiling for 3 hours, the benzene is distilled off in vacuo. The residue is dissolved in 5 ml of water, made alkaline with a 30% aqueous sodium hydroxide solution and extracted three times with 50 ml of chloroform each. The chloroform extracts are united, dried over sodium sulfate and evaporated. The residue is washed with some cold ethanol and recrystallized from ethanol. Thus 3.0 g of the title compound are obtained in the form of white crystals. Yield 37.5%. Mp.: 178° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. distillationthe benzene is distilled off in vacuo
  3. dissolutionThe residue is dissolved in 5 ml of water
  4. extractionextracted three times with 50 ml of chloroform each
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. washThe residue is washed with some cold ethanol
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f7dccf523d4a4a91850e9e8a055ecc17
Source dataset
uspto-grants-1985_08
Patent number
US04537895

Reaction notes

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