Methyl iodide → HCID 22750693, compound

HRID 1606123Notes

Reaction equation

HRID 1606123 reaction equation
CI.Cl[CH2:4][CH2:5][CH2:6][N:7]([CH3:9])[CH3:8].[CH3:10][C:11]1[C:21]2[CH:20]=[CH:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16](=[O:26])[C:15]=2[CH:14]=[CH:13][CH:12]=1.[Cl-].[NH4+]>CCOCC>[CH3:10][C:11]1[C:21]2[CH:20]=[CH:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16]([CH2:4][CH2:5][CH2:6][N:7]([CH3:9])[CH3:8])([OH:26])[C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 200675891-Methyl-5H-dibenzo[a,d]cyclohepten-5-one

Product 1

HCID 22750693HCID 22750693, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
45 °C

Procedure

20 g. of Gilman alloy are covered with 40 ml. of dry ether and treated with 0.5 ml. of methyl iodide. After the vigorous reaction has subsided somewhat, a solution containing 80 ml. of 1chloro-3-dimethylaminopropane in 360 ml. of dry ether is added dropwise in such a way that the reaction mixture is maintained at boiling. The mixture is stirred at 45° C. under reflux conditions for an additional 5 hours. The reaction mixture is then cooled with ice-water and a solution containing 43.6 g. of 1-methyl-5H-dibenzo[a,d]cyclohepten-5-one in 820 ml. of dry ether is added over a one-hour period. Subsequently, the mixture is boiled and stirred at reflux for another 17 hours. After about 12 hours, it is once more cooled with ice water and decomposed with a cold saturated ammonium chloride solution. The organic layer is separated, washed with water, dried over sodium sulfate and evaporated. The 1-methyl-5-(3-dimethylaminopropyl)-5-hydroxy-5H-dibenzo[a,d]cycloheptene obtained is recrystallized from high-boiling petroleum ether and has a melting point of 141°-143° C.

Workup

  1. customAfter the vigorous reaction
  2. additiona solution containing 80 ml
  3. temperatureis maintained
  4. additiona solution containing 43.6 g
  5. stirringstirred
  6. temperatureat reflux for another 17 hours
  7. waitAfter about 12 hours
  8. customThe organic layer is separated
  9. washwashed with water
  10. dry with materialdried over sodium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-7c9e0121a333407fa11eee03c5413e63
Source dataset
uspto-grants-1976_04
Patent number
US03952017

Reaction notes

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