Hydrochloric Acid → N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(4-chlorophenyl)ethylamine hydrochloride

HRID 972343Notes

Reaction equation

HRID 972343 reaction equation
Cl.C([N:9]([CH2:22][CH:23]([OH:31])[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)C1C=CC=CC=1.C(OCC)(=O)C>CO.[Pd]>[ClH:30].[CH3:21][O:20][C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][NH:9][CH2:22][CH:23]([OH:31])[C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21450201N-benzyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(4-chlorophenyl)ethylamine

Product 1

HCID 21406668N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(4-chlorophenyl)ethylamine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Similarly, 5.42 g. (0.02 mol) of N-benzyl-3,4-dimethoxyphenethylamine and 4.64 g. (0.03 mol) of p-chlorostyrene oxide are reacted in methanol to give N-benzyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(4-chlorophenyl) ethylamine. The hydrochloride of this ethylamine is dissolved in methanol and hydrogenated with 0.5 g. of 10% palladium-on-carbon in 10 ml. of ethyl acetate at room temperature and 60 psi. for about 90 minutes. The filtered reaction mixture is evaporated in vacuo to yield N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(4-chlorophenyl)ethylamine hydrochloride, m.p. 167°-171° C.

Workup

  1. customat room temperature
  2. customThe filtered reaction mixture
  3. customis evaporated in vacuo

Sources & evidence

ORD record
ord-3a81426ea41342ba8cc284526afb14bc
Source dataset
uspto-grants-1977_10
Patent number
US04052506

Reaction notes

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