Methyl iodide → HCID 53836108, compound

HRID 2163628Notes

Reaction equation

HRID 2163628 reaction equation
CI.Cl[CH2:4][CH2:5][CH2:6][N:7]([CH3:9])[CH3:8].[CH3:10][C:11]1[C:21]2[CH2:20][CH2:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16](=O)[C:15]=2[CH:14]=[CH:13][CH:12]=1.[Cl-].[NH4+]>CCOCC>[CH3:10][C:11]1[C:21]2[CH2:20][CH2:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16](=[CH:4][CH2:5][CH2:6][N:7]([CH3:9])[CH3:8])[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 20067572HCID 20067572, compound

Product 1

HCID 53836108HCID 53836108, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
45 °C

Procedure

10 g. of Gilman alloy are covered with 30 ml. of dry ether and treated with 0.5 ml. of methyl iodide. After the vigorous reaction has subsided somewhat, 40 ml. of 1-chloro-3-dimethylaminopropane in 120 ml. of dry ether are added dropwise in such a way that the reaction mixture is maintained at boiling. The mixture is heated at 45° C. under reflux conditions for an additional 3 hours, then cooled with ice water and treated dropwise over a period of one hour with a solution of 21.8 g. of 1-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one (J. Med. Pharm. Chem. 4, 335-49, 1961) in 400 ml. of dry ether. Subsequently, the mixture is stirred at 45° C. under reflux conditions for an additional 10 hours, then cooled with ice water and decomposed with a cold saturated ammonium chloride solution. The organic layer is removed by separation. The aqueous phase is shaken twice with 100 ml. portions of ether and the combined ether extracts are dried over sodium sulfate and evaporated. The residual 1-methyl-10,11-dihydro-5-(3-dimethylaminopropyl)-5-hydroxy-5H-dibenzo[a,d]cycloheptene has a melting point of 154°-155° C. after recrystallization from high-boiling petroleum ether.

Workup

  1. customAfter the vigorous reaction
  2. temperatureis maintained
  3. additiontreated dropwise over a period of one hour with a solution of 21.8 g
  4. customThe organic layer is removed by separation
  5. stirringThe aqueous phase is shaken twice with 100 ml
  6. dry with materialportions of ether and the combined ether extracts are dried over sodium sulfate
  7. customevaporated
  8. customafter recrystallization from high-boiling petroleum ether

Sources & evidence

ORD record
ord-c4af4dccc0214b8f8a2273b694753b63
Source dataset
uspto-grants-1979_01
Patent number
US04136116

Reaction notes

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