Water → 2,3,4,5-tetrahydro-1H-1-benzazepine

HRID 1725363Notes

Reaction equation

HRID 1725363 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:13](=O)[CH2:12][CH2:11][CH2:10][C:9]2[CH:15]=[CH:16][CH:17]=[CH:18][C:8]1=2.O.[OH-].[Na+]>O1CCCC1>[NH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2[CH:15]=[CH:16][CH:17]=[CH:18][C:8]1=2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Add 80 mL of lithium aluminum hydride (1 M solution in tetrahydrofuran) to a solution of 1,3,4,5-tetrahydrobenzo-[b]azepin-2-one (12.9 g, 80.0 mmol) in 720 mL of tetrahydro-furan. Stir the reaction mixture at reflux for 3 hours and cool to 0° C. Quench the reaction by the sequential addition of 3 mL of water, 3 mL of 15% sodium hydroxide, and 9 mL of water. Filter the resulting suspension through Celite and rinse the filter cake with ethyl acetate. Concentrate the filtrate under reduced pressure to provide the desired compound as an orange solid (10.0 g, 85%).

Workup

  1. temperatureat reflux for 3 hours
  2. customQuench
  3. customthe reaction
  4. filtrationFilter the resulting suspension through Celite
  5. washrinse the filter cake with ethyl acetate
  6. concentrationConcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-55e9d00d41de47a795bfa35516545644
Source dataset
uspto-grants-2009_02
Patent number
US07491716B2

Reaction notes

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