HCID 22765876, compound → Mabuterol hydrochloride

HRID 1111937Notes

Reaction equation

HRID 1111937 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH:12]([OH:26])[CH2:13][N:14](CC2C=CC=CC=2)[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][C:3]=1[Cl:27].[H][H]>CO.Cl.[Pd]>[ClH:27].[NH2:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5]([CH:12]([OH:26])[CH2:13][NH:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[CH:4][C:3]=1[Cl:27]

Participants

6

Reactant 2

HCID 22765876HCID 22765876, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 6917754Mabuterol hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

0.76 gm of 1-(4'-amino-3'-chloro-5'-trifluoromethyl-phenyl)-2-(N-benzyl-N-tert.butylamino)-ethanol were dissolved in 20 ml of methanol and 1.95 ml of 1N hydrochloric acid, and the solution was hydrogenated in a hydrogenation vessel in the presence of 80 mgm of palladium/coal-catalyst (10%) until 1 mol of hydrogen had been absorbed. Afterwards, the catalyst was removed by filtration, and the filtrate was evaporated to dryness in vacuo. The oily residue was purified by column chromatography (silicagel; chloroform:methanol:concentrated ammonia = 80:20:1 as eluant). The fractions containing the desired substance were combined, and the solvent was removed in vacuo. The remaining crystalline base of the desired compound was converted into its hydrochloride with the calculated quantity of 1.07 N hydrochloric acid in isopropanol, and recrystallized from ethyl acetate/ether. M.p. 205°-207° C. (decomp.).

Workup

  1. customhad been absorbed
  2. customAfterwards, the catalyst was removed by filtration
  3. customthe filtrate was evaporated to dryness in vacuo
  4. customThe oily residue was purified by column chromatography (silicagel; chloroform:methanol:concentrated ammonia = 80:20:1 as eluant)
  5. additionThe fractions containing the desired substance
  6. customthe solvent was removed in vacuo
  7. customrecrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-5f62d17c018040ed8ea12e06c83d9746
Source dataset
uspto-grants-1978_10
Patent number
US04119710

Reaction notes

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