HCID 14502069, compound → HCID 14502070, compound

HRID 1089677Notes

Reaction equation

HRID 1089677 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH:10]([NH:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH2:9][CH2:8][C:7]=2[CH:20]=1>[OH-].[Na+].C(O)C>[F:1][C:2]([F:21])([F:22])[C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH:10]([NH:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:9][CH2:8][C:7]=2[CH:20]=1

Participants

4

Reactant 1

HCID 14502069HCID 14502069, compound

Product 1

HCID 14502070HCID 14502070, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

315.34 g (1 mol) of 2-trifluoromethyl-7-(N-ethoxycarbonylmethylamino)-6,7,8,9-tetrahydro-[5H]-benzocycloheptene are heated at reflux for approximately 25 minutes in a mixture of 1000 ml of normal sodium hydroxide and 2200 ml of ethanol. The ethanol is then distilled off terminating under reduced pressure, and the aqueous phase is washed twice with 4000 ml of diethyl ether each time. The ethereal phases are washed with water again. 1000 ml of a normal hydrochloric acid solution are added to the combined aqueous phases. The precipitate obtained is collected and washed. 250 g of 2-trifluoromethyl-7-(N-carboxymethylamino)-6,7,8,9-tetrahydro-[5H]-benzocycloheptene are obtained, which sublimes above 260° C. (Yield 87%). By adding a stoichiometric amount of hydrochloric acid and recrystallising from water, the hydrochloride of this amino acid, which sublimes towards 220°-222° C., is obtained.

Workup

  1. distillationThe ethanol is then distilled off
  2. customterminating under reduced pressure
  3. washthe aqueous phase is washed twice with 4000 ml of diethyl ether each time
  4. washThe ethereal phases are washed with water again
  5. addition1000 ml of a normal hydrochloric acid solution are added to the combined aqueous phases
  6. customThe precipitate obtained
  7. customis collected
  8. washwashed

Sources & evidence

ORD record
ord-de3cce67791e439596a252839f072474
Source dataset
uspto-grants-1992_01
Patent number
US05079245

Reaction notes

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