Methanol → HCID 21502282, compound

HRID 917845Notes

Reaction equation

HRID 917845 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH:12]=[C:11](N3CCCCC3)[C:10]3[CH:25]=[CH:26][CH:27]=[CH:28][C:9]2=3)[CH2:4][CH2:3]1.C[OH:30]>O>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][C:11](=[O:30])[C:10]3[CH:25]=[CH:26][CH:27]=[CH:28][C:9]2=3)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 887MethanolHCID 21502279HCID 21502279, compound

Product 1

HCID 21502282HCID 21502282, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This enamine product is then hydrolyzed by refluxing with stirring in 150 ml. 10% in water and 75 ml. of methanol. The methanol is then removed by evaporation of the reaction mixture on a rotary evaporator. The residual material containing the desired product is made alkaline by adding solid NaHCO3 until no more CO2 is evolved. The residue is then extracted with toluene and ether. The combined extracts containing the product are dried over anhydrous MgSO4, filtered, and the solvents removed with a rotary evaporator. There remains a dark brown residual oil which when seeded crystallizes slowly. This product is collected and recrystallized from hexane two times to give 1-methyl-4-(10,11-dihydro-10-oxo-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, m.p. 138°-140°C. Three more recrystallizations from hexane gives product, m.p. 141°-142°C.

Workup

  1. temperatureby refluxing
  2. customThe methanol is then removed by evaporation of the reaction mixture on a rotary evaporator
  3. additionThe residual material containing the desired product
  4. additionby adding solid NaHCO3 until no more CO2
  5. extractionThe residue is then extracted with toluene and ether
  6. additionThe combined extracts containing the product
  7. dry with materialare dried over anhydrous MgSO4
  8. filtrationfiltered
  9. customthe solvents removed with a rotary evaporator
  10. customseeded crystallizes slowly
  11. customThis product is collected
  12. customrecrystallized from hexane two times

Sources & evidence

ORD record
ord-7c332479973e49ddaee9132440f67655
Source dataset
uspto-grants-1976_07
Patent number
US03968115

Reaction notes

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