Dimethyl Sulfate → HCID 12319500, compound

HRID 1077331Notes

Reaction equation

HRID 1077331 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:8]2)[CH2:4][CH2:3]1.O1CCC[CH2:23]1.C([Li])CCC.COS(OC)(=O)=O>CCCCCC>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH3:23])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:8]2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 8028Tetrahydrofuran2×HCID 12213082HCID 12213082, compoundHCID 178418339Butyllithium

Product 1

HCID 12319500HCID 12319500, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 1.4 g. of 1,3-dihydro-1'-methyl-3-phenylspiro[isobenzofuran-1,4'-piperidine], (Example 2), in 20 ml. of tetrahydrofuran is cooled to -50° and treated dropwise with 4 ml. of butyllithium in hexane. Stirring is continued for 30 minutes under nitrogen. To the solution is slowly added 900 mg. of dimethylsulfate in 10 ml. of tetrahydrofuran. The mixture is stirred at -10° for 1 hour and overnight at ambient temperature. Ice is added, the mixture is extracted with ether, and the organic solution is concentrated to an oil. The oil is converted to the hydrobromide salt and recrystallized from ethyl acetate to give crystals, m.p. 122°-125°.

Workup

  1. additiontreated dropwise with 4 ml
  2. stirringThe mixture is stirred at -10° for 1 hour and overnight at ambient temperature
  3. additionIce is added
  4. extractionthe mixture is extracted with ether
  5. concentrationthe organic solution is concentrated to an oil
  6. customrecrystallized from ethyl acetate
  7. customto give crystals, m.p. 122°-125°

Sources & evidence

ORD record
ord-48f40609b68245539fb78a6bfce2a9dc
Source dataset
uspto-grants-1976_05
Patent number
US03959475

Reaction notes

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