Ethyl bromoacetate → HCID 14502069, compound

HRID 1089676Notes

Reaction equation

HRID 1089676 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8][C:7]=2[CH:14]=1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>C1C=CC=CC=1>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH:10]([NH:13][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:9][CH2:8][C:7]=2[CH:14]=1

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 14502066HCID 14502066, compound

Product 1

HCID 14502069HCID 14502069, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

458.5 g (2 mols) of 2-trifluoromethyl-7-amino-6,7,8,9-tetrahydro-[5H]-benzocycloheptene are dissolved in 2000 ml of anhydrous benzene. One mol of ethyl bromoacetate is added thereto and the whole is heated under reflux. A precipitate forms. The refluxing is maintained for 4 hours, then the mixture is allowed to return to room temperature. The hydrobromide precipitate of the starting amine is filtered off and washed in benzene then ether. The solvent is distilled off from the filtrate. The oil obtained is used as such for the subsequent hydrolysis. Ultimately 271 g of 2-trifluoromethyl-7-(N-ethoxycarbonylmethylamino)-6,7,8,9-tetrahydro-[5H]-benzocycloheptene are obtained. (Yield 86%), a sample of which is purified in the form of the hydrochloride, which sublimes towards 270°-280° C.

Workup

  1. temperaturethe whole is heated
  2. temperatureunder reflux
  3. temperatureThe refluxing is maintained for 4 hours
  4. customto return to room temperature
  5. filtrationThe hydrobromide precipitate of the starting amine is filtered off
  6. washwashed in benzene
  7. distillationThe solvent is distilled off from the filtrate
  8. customThe oil obtained
  9. customsuch for the subsequent hydrolysis

Sources & evidence

ORD record
ord-a1dab7a3a0b14e6ca67563fdbfff281e
Source dataset
uspto-grants-1992_01
Patent number
US05079245

Reaction notes

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