Benzene → HCID 70603592, compound

HRID 2163634Notes

Reaction equation

HRID 2163634 reaction equation
[CH3:1][C:2]1[C:12]2[CH:11]=[CH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7]([CH2:18][CH2:19][CH2:20][N:21](C)C)([OH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26].[CH:30]1C=CC=CC=1>>[CH3:1][C:2]1[C:12]2[CH:11]=[CH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7]([CH2:18][CH2:19][CH2:20][NH:21][C:25]([O:27][CH2:28][CH2:29][CH3:30])=[O:26])([OH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 241Benzene2×HCID 10928Ethyl chloroformateHCID 22750693HCID 22750693, compound

Product 1

HCID 70603592HCID 70603592, compound

Conditions

Temperature
20 °C

Procedure

A solution containing 30 g. of 1-methyl-5-(3-dimethylaminopropyl)-5-hydroxy-5H-dibenzo[a,d]cycloheptene in 100 ml. of dry benzene is added dropwise with stirring at 20° C. to a mixture of 31.8 g. of ethyl chloroformate in 100 ml. of dry benzene. Subsequently, the mixture is vigorously boiled under reflux conditions for 20 hours. After cooling, the benzene solution is washed with water, dilute hydrochloric acid and once again with water, dried over sodium sulfate and evaporated. The 1-methyl-5-(3-methylcarbethoxyaminopropyl)-5-hydroxy-5H-dibenzo [a,d]cycloheptene obtained has a melting point of 157°-159° C. after recrystallization from ethanol.

Workup

  1. additionA solution containing 30 g
  2. temperatureAfter cooling
  3. washthe benzene solution is washed with water, dilute hydrochloric acid and once again with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-ee4794029ebf4cb9a49c5d7f6b8025db
Source dataset
uspto-grants-1979_01
Patent number
US04136116

Reaction notes

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