Water → 3-Chloro-5-(3-chloropropyl)-10,11-dihydro-5H-dibenzo[b,f]azepine

HRID 1166424Notes

Reaction equation

HRID 1166424 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][CH2:8][CH2:9][C:10]([N:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][CH2:15][C:14]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:13]1=2)=O.O.[OH-].[Na+]>O1CCCC1>[Cl:27][C:25]1[CH:24]=[CH:23][C:14]2[CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:12]([CH2:10][CH2:9][CH2:8][Cl:7])[C:13]=2[CH:26]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22998298HCID 22998298, compound

Product 1

HCID 229983063-Chloro-5-(3-chloropropyl)-10,11-dihydro-5H-dibenzo[b,f]azepineYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0 M solution of lithiumaluminium hydride in tetrahydrofuran (18.7 ml, 18.7 mmol) was introduced into a 250 ml dry, three-necked, roundbottom flask under a nitrogen atmosphere. The solution was cooled on an icebath. Concentrated sulphuric acid (0.5 ml) was added dropwise, with caution, over 10 minutes. More dry tetrahydrofuran (20 ml) was added to compensate for evaporated solvent and the mixture was stirred for 15 minutes. Additional tetrahydrofuran was added (20 ml) and the icebath was removed. The mixture was stirred for 75 minutes at room temperature. The above amide (3.0 g, 9.3 mmol) was dissolved in dry tetrahydrofuran (25 ml) and dropwise added over 20 minutes. The reaction mixture was stirred for 1 h. Water (0.7 ml) was added, followed subsequently by 4 N sodium hydroxide (0.7 ml) and water (2.1 mi). Stirring was continued for 30 minutes. The mixture was filtered (hyflo) and evaporated in vacuo, affording 2.70 g (95%) 3-chloro-5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine as an oil.

Workup

  1. customdry
  2. temperatureThe solution was cooled on an icebath
  3. additionConcentrated sulphuric acid (0.5 ml) was added dropwise, with caution, over 10 minutes
  4. additionMore dry tetrahydrofuran (20 ml) was added
  5. customfor evaporated solvent
  6. additionAdditional tetrahydrofuran was added (20 ml)
  7. customthe icebath was removed
  8. stirringThe mixture was stirred for 75 minutes at room temperature
  9. additiondropwise added over 20 minutes
  10. stirringThe reaction mixture was stirred for 1 h
  11. stirringStirring
  12. waitwas continued for 30 minutes
  13. filtrationThe mixture was filtered (hyflo)
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-3450cf715af34738aa4206eff544dd63
Source dataset
uspto-grants-2003_09
Patent number
US06613791B1

Reaction notes

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