Ethyl chloroformate → HCID 20359366, compound

HRID 1730104Notes

Reaction equation

HRID 1730104 reaction equation
[CH3:1][N:2](C)[CH2:3][CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[CH2:16])[C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=2[CH2:6]1.C(OC([Cl:27])=O)C.[OH-].[K+]>C1(C)C=CC=CC=1>[ClH:27].[CH3:1][NH:2][CH2:3][CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[CH2:16])[C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=2[CH2:6]1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 547246HCID 547246, compound

Product 1

HCID 20359366HCID 20359366, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 15.2 g. (0.055 mole) of 10-(2-dimethylaminoethyl)-10,11-dihydro-5-methylene-5H-dibenzo[a,d]cycloheptene and 23.6 g. (0.218 mole) of ethylchloroformate in 125 ml. of toluene is refluxed under a nitrogen atmosphere for 18 hours. The excess solvent and reagent is removed by evaporation in vacuo. The resulting oil product is dissolved in a solution of 175 ml. of ethanol, 17 ml. of water and 35 g. (0.625 mole) of potassium hydroxide and refluxed for 10 hours. The solvents are removed in vacuo and the resulting layers are separated between ether and water. The ether is then extracted twice with 2N hydrochloric acid and the resulting aqueous acid is then made basic and extracted with ether. The excess solvent is then dried and evaporated and the resulting oil is dissolved in isopropyl alcohol and treated with hydrochloric gas. The residue is then filtered and recrystallized from isopropyl alcohol to give 10-(2-methylaminoethyl)-10,11-dihydro-5-methylene-5H-dibenzo[a,d]cycloheptene hydrochloride, m.p. 176°-177° C.

Workup

  1. additionA mixture of 15.2 g
  2. customThe excess solvent and reagent is removed by evaporation in vacuo
  3. dissolutionThe resulting oil product is dissolved in a solution of 175 ml
  4. customThe solvents are removed in vacuo
  5. customthe resulting layers are separated between ether and water
  6. extractionThe ether is then extracted twice with 2N hydrochloric acid
  7. extractionextracted with ether
  8. customThe excess solvent is then dried
  9. customevaporated
  10. dissolutionthe resulting oil is dissolved in isopropyl alcohol
  11. additiontreated with hydrochloric gas
  12. filtrationThe residue is then filtered
  13. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-2666aea3bfd14aaeafea2f0b4b1f79ca
Source dataset
uspto-grants-1976_11
Patent number
US03991102

Reaction notes

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