Dibenzosuberol → Oxitriptyline

HRID 1900249Notes

Reaction equation

HRID 1900249 reaction equation
[H-].[Na+].[CH2:3]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([OH:18])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.Cl[CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22]>CCCCCC.CCOCC>[CH:16]1[C:17]2[CH2:3][CH2:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[CH:11]([O:18][CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 14588DibenzosuberolHCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamide

Product 1

HCID 34624OxitriptylineYield 72.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Procedure

Washed sodium hydride (2.6 g, 64.6 mmol, 60 weight % in oil) two times with hexane under a nitrogen atmosphere. Added 50 mL of dry ether, and then added dibenzosuberol (13.6 g, 64.6 mmol) dissolved in 30 mL of dry ether followed by 2-chloro-N,N-dimethylacetamide (7.8 g, 64.6 mmol) dissolved in 20 mL of dry ether. Stirred at room temperature for 16 hours. Added water, and separated layers. Evaporated the organic solution, and triturated the residue with carbon tetrachloride and hexane. Filtered the white solid to give 13.79 g (72% yield) of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl-oxy-N,N-dimethylacetamide.

Workup

  1. customAdded water, and separated layers
  2. customEvaporated the organic solution
  3. customtriturated the residue with carbon tetrachloride and hexane
  4. filtrationFiltered the white solid

Sources & evidence

ORD record
ord-ba38d220116b4c5a8607969808d79758
Source dataset
uspto-grants-1996_11
Patent number
US05574173

Reaction notes

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