Triethylamine → 1-(3-Chlorophenoxy)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 2107694Notes

Reaction equation

HRID 2107694 reaction equation
[C:1](O)(=O)C(O)=O.[Cl:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[O:11][CH:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][CH2:15][NH:14][CH2:13]1.C(N(CC)CC)C.ClC(OCC)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(Cl)(Cl)Cl.O1CCCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[O:11][CH:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][CH2:15][N:14]([CH3:1])[CH2:13]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14348993HCID 14348993, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 143489961-(3-Chlorophenoxy)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of 1-(m-chlorophenoxy)-2,3,4,5-tetrahydro-3-benzazepine of Example 4, (6.5 g, 0.024 mole) and triethylamine (2.8 g, 0.028 mole) in chloroform (75 ml) was slowly dropped ethyl chloroformate (3.0 g, 0.028 mole) in chloroform (10 ml.). The reaction mixture was stirred overnight, about 16 hours, at ambient temperature, then was concentrated to an oil which was dissolved in ether, washed with water, dilute HCl, again twice washed with water, then dried (saturated NaCl, anhydrous MgSO4). The solution was filtered, then concentrated to an oil (7.5 g, 90%). A solution of the oil in tetrahydrofuran (THF) (75 ml) was slowly dropped into a refluxing suspension of LiAlH4 (1.6 g. 0.042 mole) in THF (125 ml). After refluxing five hours, the mixture was cooled, then was quenched by dropwise addition of saturated NH4Cl solution. The mixture was diluted with ether, filtered, washed twice with water then dried (saturated NaCl, anhydrous MgSO4). The solution was filtered, then concentrated to an oil (5.6 g., 93%). This oil was distilled to yield an oil of 1-(m-chlorophenoxy)-3-methyl-2,3,4,5-tetrahydro-3-benzazepine (150°-170° C./0.1 mm).

Workup

  1. concentrationwas concentrated to an oil which
  2. dissolutionwas dissolved in ether
  3. washwashed with water, dilute HCl
  4. washagain twice washed with water
  5. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  6. filtrationThe solution was filtered
  7. concentrationconcentrated to an oil (7.5 g, 90%)
  8. temperatureAfter refluxing five hours
  9. temperaturethe mixture was cooled
  10. customwas quenched by dropwise addition of saturated NH4Cl solution
  11. additionThe mixture was diluted with ether
  12. filtrationfiltered
  13. washwashed twice with water
  14. dry with materialthen dried (saturated NaCl, anhydrous MgSO4)
  15. filtrationThe solution was filtered
  16. concentrationconcentrated to an oil (5.6 g., 93%)
  17. distillationThis oil was distilled

Sources & evidence

ORD record
ord-65918db28b2142c7981b3758a9fedfc0
Source dataset
uspto-grants-1990_06
Patent number
US04935418

Reaction notes

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