Aniline → HCID 21276860, compound

HRID 2292112Notes

Reaction equation

HRID 2292112 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[C:4]([CH2:10][CH2:11]Cl)[CH:3]=1.[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:3]=[C:4]2[C:5](=[CH:8][CH:9]=1)[CH2:6][N:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][CH2:10]2

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 21276868HCID 21276868, compound

Product 1

HCID 21276860HCID 21276860, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-chloro-2-(2-chloroethyl)benzyl chloride (5 g), aniline (2.1 g) and triethylamine (5.7 g), were dissolved in chloroform (40 ml) and the mixture heated at reflux for 18 hr. The reaction mixture was cooled and washed with 2M sodium hydroxide solution (100 ml), 2M hydrochloric acid (100 ml) and water (100 ml), then dried (sodium sulphate) and evaporated to dryness in vacuo. The residue was chromatographed on silica gel to give the product, 6-chloro-2-phenyl-1,2,3,4-tetrahydroisoquinoline m.pt. 67°-70°.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 hr
  3. temperatureThe reaction mixture was cooled
  4. washwashed with 2M sodium hydroxide solution (100 ml), 2M hydrochloric acid (100 ml) and water (100 ml)
  5. dry with materialdried (sodium sulphate)
  6. customevaporated to dryness in vacuo
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-d0335b9088e54640ba722d35cb8e927f
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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