Potassium Sodium Tartrate → 2,3,4,5-tetrahydro-1H-1-benzazepine

HRID 1266093Notes

Reaction equation

HRID 1266093 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][C:2]1=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.CCOCC>[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (2.71 g, 16.7 mmol) in THF (40 mL) was added dropwise to a suspension of LAH (1.27 g, 33.4 mmol) in ether (150 mL) at room temperature. The mixture was refluxed for 16 h. Saturated Rochelle's salt solution (15 mL) was added to the mixture cooled with an ice-water bath. The mixture was stirred for 2 hrs and the two layers were separated. The aqueous layer was extracted with ether (2×25 mL). The combined organic layer was dried (Na2SO4), concentrated in vacuo and flash column chromatography (EtOAc:hexane/3:7) gave 2,3,4,5-tetrahydro-1H-1-benzazepine (2.40 g, 98%) as a yellow liquid. 1H NMR (CDCl3, 300 MHz) δ1.58-1.70 (m, 2H), 1.72-1.86 (m, 2H), 2.72-2.82 (m, 2H), 3.00-3.10 (m, 2H), 3.78 (br, 1H), 6.74 (dd, J=1.1, 7.7 Hz, 1H), 6.82 (td, J=7.3, 1.1 Hz, 1H), 7.04 (td, J=7.5, 1.5 Hz, 1H), 7.11 (d, J=7.4 Hz, 1H) ppm.

Workup

  1. temperatureThe mixture was refluxed for 16 h
  2. temperaturecooled with an ice-water bath
  3. customthe two layers were separated
  4. extractionThe aqueous layer was extracted with ether (2×25 mL)
  5. dry with materialThe combined organic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo and flash column chromatography (EtOAc:hexane/3:7)

Sources & evidence

ORD record
ord-20b30a1c1f8346cfa0751405bbd1d923
Source dataset
uspto-grants-2003_04
Patent number
US06548493B1

Reaction notes

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