Ammonia → 1-(4'-Amino-3'-trifluoromethyl-phenyl)-2-tert.pentylamino-ethanol hydrobromide

HRID 1111938Notes

Reaction equation

HRID 1111938 reaction equation
Cl.[NH2:2][C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:6]([CH:13]([OH:21])[CH2:14][NH:15][C:16]([CH2:19][CH3:20])([CH3:18])[CH3:17])=[CH:5][C:4]=1[Br:22].N.[H][H]>C(OCC)(=O)C>[BrH:22].[NH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH:13]([OH:21])[CH2:14][NH:15][C:16]([CH2:19][CH3:20])([CH3:17])[CH3:18])=[CH:7][C:8]=1[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 133556401-(4'-Amino-3'-bromo-5'-trifluoromethyl-phenyl)-2-tert.pentylamino-ethanol hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 133557631-(4'-Amino-3'-trifluoromethyl-phenyl)-2-tert.pentylamino-ethanol hydrobromide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5 gm of 1-(4'-amino-3'-bromo-5'-trifluoromethyl-phenyl)-2-tert.pentylamino-ethanol hydrochloride were distributed between ethyl acetate and 2N ammonia. The organic layer was dried and evaporated in vacuo, the residual base was dissolved in 100 ml of methanol in a hydrogenation vessel. 2.5 gm of palladium oxide/barium sulfate catalyst (5%) were added, and the mixture was hydrogenated until 1 mol of hydrogen had been absorbed. After the catalyst had been removed by filtration, the filtrate was evaporated in vacuo, and the solid residue was recrystallized from isopropanol. The obtained hydrobromide melted at 174°-175° C. (decomp.).

Workup

  1. customThe organic layer was dried
  2. customevaporated in vacuo
  3. dissolutionthe residual base was dissolved in 100 ml of methanol in a hydrogenation vessel
  4. addition2.5 gm of palladium oxide/barium sulfate catalyst (5%) were added
  5. customhad been absorbed
  6. customAfter the catalyst had been removed by filtration
  7. customthe filtrate was evaporated in vacuo
  8. customthe solid residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-630efa2be383451c87d948a961490177
Source dataset
uspto-grants-1978_10
Patent number
US04119710

Reaction notes

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