Hydrochloric Acid → HCID 23457306, compound

HRID 1680178Notes

Reaction equation

HRID 1680178 reaction equation
C(N(CC)CC)C.[CH3:8][N:9](C)[CH2:10][CH2:11][C@H:12]1[C@H:20]([CH3:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.ClC(OCC)=O.Cl>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:21][CH:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:12]1[CH2:11][CH2:10][NH:9][CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformate2×HCID 70576522HCID 70576522, compound

Product 1

HCID 23457306HCID 23457306, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

7.5 ml of triethylamine are added to a solution of 5.0 g of trans-2-(2-dimethylaminoethyl)-3-methyl-1-phenylindoline in 36 ml of toluene. 2.6 ml of ethyl chloroformate are added dropwise whilst refluxing the reaction mixture. After one and two hours 2.6 ml of ethyl chloroformate are again added. After a reaction time of 3 hours, cooling is effected and the reaction mixture is distributed between methylene chloride and dilute hydrochloric acid. After the mixture is washed with water and dried over sodium sulphate, the solvent is removed, whereupon the ethyl carbamate of the trans-3-methyl-2-(2-methylaminoethyl)-1-phenylindoline remains as a brown oil. 2. The latter is dissolved in 17 ml of n-butanol. 3.5 g of pulverized potassium hydroxide are added. The mixture is heated for 4 hours in an oil bath at 110°.

Workup

  1. temperaturewhilst refluxing the reaction mixture
  2. temperatureAfter a reaction time of 3 hours, cooling
  3. washAfter the mixture is washed with water
  4. dry with materialdried over sodium sulphate
  5. customthe solvent is removed, whereupon the ethyl carbamate of the trans-3-methyl-2-(2-methylaminoethyl)-1-phenylindoline
  6. dissolutionThe latter is dissolved in 17 ml of n-butanol
  7. addition3.5 g of pulverized potassium hydroxide are added
  8. temperatureThe mixture is heated for 4 hours in an oil bath at 110°

Sources & evidence

ORD record
ord-5aa96161546b4458beadc65f58af0dd4
Source dataset
uspto-grants-1981_06
Patent number
US04272533

Reaction notes

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