Aniline → HCID 11321753, compound

HRID 2292107Notes

Reaction equation

HRID 2292107 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Cl.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:13]1([N:12]2[CH2:2][CH2:3][C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 15122692HCID 15122692, compound

Product 1

HCID 11321753HCID 11321753, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2-(2-chloroethyl)benzyl chloride (19 g), aniline (9.3 g), and triethylamine (22.22 g,) in chloroform (80 ml) was heated at reflux for 6 hrs. The reaction mixture was cooled and washed with 2M sodium hydroxide solution (3×100 ml). The chloroform layer was dried (magnesium sulphate) and evaporated in vacuo. The residue was distilled in vacuo to afford 2-phenyl-1,2,3,4-tetrahydroisoquinoline (6.2 g. b.pt. 112°-113°/0.08-0.1 mmHg) characterised by its nmr spectrum.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hrs
  3. temperatureThe reaction mixture was cooled
  4. washwashed with 2M sodium hydroxide solution (3×100 ml)
  5. dry with materialThe chloroform layer was dried (magnesium sulphate)
  6. customevaporated in vacuo
  7. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-fe21b100126948de8be620d0ad023623
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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