Aniline → HCID 21276866, compound

HRID 2292115Notes

Reaction equation

HRID 2292115 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH2:11]Cl)=[C:6]([CH:9]=1)[CH2:7]Cl.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:9]=[C:6]2[C:5]([CH2:10][CH2:11][N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:7]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 21276879HCID 21276879, compound

Product 1

HCID 21276866HCID 21276866, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-Chloro-2-(2-chloroethyl)benzyl chloride (8 g), was dissolved in chloroform (50 ml), then aniline (2.79 g,) and triethylamine (8.01 g,) were added to the solution. The mixture was refluxed for 18 hr. then cooled and washed with 2M sodium hydroxide solution (2×100 ml). The chloroform layer was dried (magnesium sulphate) and evaporated in vacuo. The residue was distilled in vacuo to afford 7-chloro-2-phenyl-1,2,3,4-tetrahydroisoquinoline (1.35 g), b.pt. 170°-180°/0.6-0.8 mmHg) characterised by its nmr spectrum.

Workup

  1. temperatureThe mixture was refluxed for 18 hr
  2. temperaturethen cooled
  3. washwashed with 2M sodium hydroxide solution (2×100 ml)
  4. dry with materialThe chloroform layer was dried (magnesium sulphate)
  5. customevaporated in vacuo
  6. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-4046dd073cd4456cb8f0ea7d26a68bfc
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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