Water → HCID 20491807, compound

HRID 434704Notes

Reaction equation

HRID 434704 reaction equation
[CH3:1][Li].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:13]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)=[CH:12][C:11]3[CH:21]=[CH:22][CH:23]=[CH:24][C:10]=3[C:9](=[O:25])[C:8]=2[CH:26]=1.O>CCOCC.O1CCCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:13]([N:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)=[CH:12][C:11]3[CH:21]=[CH:22][CH:23]=[CH:24][C:10]=3[C:9]([CH3:1])([OH:25])[C:8]=2[CH:26]=1

Participants

6

Reactant 3

HCID 962WaterHCID 20491794HCID 20491794, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 20491807HCID 20491807, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Methyllithium, 35 ml. of a 1.6 M solution in ether, was added dropwise to a stirred solution of the product from Step C (18 g., 0.047 mole) in ether (200 ml) and tetrahydrofuran (60 ml) cooled in an ice bath and under nitrogen. Stirring was continued at room temperature for 3 hours. The mixture was cooled in ice and hydrolyzed by the dropwise addition of water. After dilution with ether and water, the layers were separated and the aqueous phase was re-extracted with ether. The combined ether extracts were washed with water, dried over anhydrous sodium sulfate and evaporated. The mixture of 3-bromo-5-methyl-10-(4-methylpiperazinyl)-5H-dibenzo[a,d]cyclohepten-5-ol and 3-bromo-5-methyl-11-(4-methylpiperazinyl)-5H-dibenzo[a,d]cyclohepten-5-ol was obtained as a residual dark yellow glass; yield, 18 g, (96%).

Workup

  1. temperaturecooled in an ice bath and under nitrogen
  2. customAfter dilution with ether and water, the layers were separated
  3. extractionthe aqueous phase was re-extracted with ether
  4. washThe combined ether extracts were washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. additionThe mixture of 3-bromo-5-methyl-10-(4-methylpiperazinyl)-5H-dibenzo[a,d]cyclohepten-5-ol

Sources & evidence

ORD record
ord-f2d45975abd448149d19fc920c2ba6df
Source dataset
uspto-grants-1983_08
Patent number
US04399141

Reaction notes

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