Diethyl Ether → HCID 21511024, compound

HRID 1657445Notes

Reaction equation

HRID 1657445 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[CH2:12][C:11](=[O:19])[C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]2=3)[CH2:4][CH2:3]1.CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>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][CH:11]([OH:19])[C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]2=3)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21502282HCID 21502282, compound

Product 1

HCID 21511024HCID 21511024, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of 3.0 g. (0.01 mole) of 1-methyl-4-(10,11-dihydro-10-oxo-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine (0.01 mole) in 200 ml. of dry ether is added dropwise in a dry inert atmosphere to a stirred suspension of 3.8 g. (0.1 mole) of lithium aluminum hydride. The reaction is then stirred overnight (20 hours) at room temperature under a dry inert atmosphere. Then there is added dropwise carefully with stirring 3 ml. of water followed by 3 ml. of 20% NaOH solution in water followed by 15 ml. of water. The ether solution of the product is decanted and the remaining salts washed with ether and decanted. The combined ether solutions of the product are dried over anhydrous MgSO4, filtered, and the ether evaporated on a rotary evaporator. This gives after one recrystallization from ethanol 1-methyl-4-(10,11-dihydro-10-hydroxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, m.p. 205°-206°C.

Workup

  1. additionThen there is added dropwise carefully
  2. stirringwith stirring 3 ml
  3. customThe ether solution of the product is decanted
  4. washthe remaining salts washed with ether
  5. customdecanted
  6. dry with materialThe combined ether solutions of the product are dried over anhydrous MgSO4
  7. filtrationfiltered
  8. customthe ether evaporated on a rotary evaporator
  9. customThis gives
  10. customafter one recrystallization from ethanol 1-methyl-4-(10,11-dihydro-10-hydroxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, m.p. 205°-206°C.

Sources & evidence

ORD record
ord-acd38be6624f404a86a07c728a8b776f
Source dataset
uspto-grants-1976_06
Patent number
US03960872

Reaction notes

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