Water → HCID 23324574, compound

HRID 1380892Notes

Reaction equation

HRID 1380892 reaction equation
[CH3:1][O:2][C:3]1[C:33]([O:34][CH3:35])=[CH:32][C:6]2[CH2:7][C:8](=[O:31])[N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:30])[CH:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][C:20]([O:28][CH3:29])=[C:21]([O:26][CH3:27])[CH:22]=4)[CH2:17]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[Se](=O)=[O:37].O>O1CCOCC1>[CH3:1][O:2][C:3]1[C:33]([O:34][CH3:35])=[CH:32][C:6]2[C:7](=[O:37])[C:8](=[O:31])[N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:30])[CH:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][C:20]([O:28][CH3:29])=[C:21]([O:26][CH3:27])[CH:22]=4)[CH2:17]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 13579649HCID 13579649, compound

Product 1

HCID 23324574HCID 23324574, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Here, 1-[7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane (1.64 g, 0.0034 mol) is added at 70° C. to a suspension of selenium dioxide (0.41 g, 0.0036 mol) and Celite (0.34 g) in 1,4-dioxan (17 ml) and water (0.68 ml) is added and the mixture is refluxed for 40 hours. After cooling, it is suction filtered, concentrated by rotary evaporation in vacuo and purified over silica gel (40 g) (32-63 μm) with methylene chloride and increasing amounts of ethanol (up to 40%). The clean fractions are concentrated by evaporation and the hydrochloride is precipitated from acetone. Yield: 0.6 g. Mp: >145° C. (decomp.).

Workup

  1. temperaturethe mixture is refluxed for 40 hours
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation in vacuo
  5. custompurified over silica gel (40 g) (32-63 μm) with methylene chloride
  6. temperatureincreasing amounts of ethanol (up to 40%)
  7. concentrationThe clean fractions are concentrated by evaporation
  8. customthe hydrochloride is precipitated from acetone

Sources & evidence

ORD record
ord-909aa004aced4a8aad892c7c58739f39
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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