Water → 2-Benzyloxy-7,8,9,10-tetrahydro-11-phenyl-6H-azepino[1,2-a]indole

HRID 66828Notes

Reaction equation

HRID 66828 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]1[CH2:18][CH2:19][CH2:20][CH2:21][C:22](=O)[C:13]1=[C:12]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[OH-].[K+].O>C(O)COCCOCCO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:13]1=[C:12]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 20529096HCID 20529096, compound

Product 1

HCID 205291872-Benzyloxy-7,8,9,10-tetrahydro-11-phenyl-6H-azepino[1,2-a]indole

Reagents, catalysts & solvents 1

HCID 8172Triethylene GlycolSolvent

Procedure

An amount of 2.3 g (6 m mole) of 2-benzyloxy-7,8,9,10-tetrahydro-10-oxo-11-phenyl-6H-azepino[1,2-a]indole 4.5 ml of 80% hydrazine hydrate and 1.5 g of potassium hydroxide were heated in 6 ml of triethylene-glycol for two hours to 180° C. and for four hours to 220° C. After cooling, the reaction mixture was mixed with water and extracted with chloroform. After evaporation of the chloroform extracts, the residue was purified by column chromatography on silicagel (solvent: toluene). When the eluates were evaporated, colorless crystals were obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with chloroform
  3. customAfter evaporation of the chloroform
  4. customthe residue was purified by column chromatography on silicagel (solvent: toluene)
  5. customWhen the eluates were evaporated
  6. customcolorless crystals were obtained

Sources & evidence

ORD record
ord-54c84805a4a74fbbbbfc6dae3c3b6578
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Reaction notes

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