Ethanol hydrochloride → HCID 22164912, compound

HRID 1032710Notes

Reaction equation

HRID 1032710 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH:12]([CH2:14][N:15]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)CC2C=CC=CC=2)[OH:13])=[CH:4][C:3]=1[Cl:37].Cl.C(O)C>C(O)C.[Pd]=O>[NH2:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5]([CH:12]([CH2:14][NH:15][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[OH:13])=[CH:4][C:3]=1[Cl:37]

Participants

5

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 221649154-Amino-3-chloro-alpha-[[[5-(2-phenylethoxy) pentyl](phenylmethyl)amino]methyl]-5-(trifluoromethyl)benzenemethanol

Product 1

HCID 22164912HCID 22164912, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-amino-3-chloro-α-[[[5-(2-phenylethoxy) pentyl](phenylmethyl)amino]methyl]-5-(trifluoromethyl)benzenemethanol (0.42 g) and conc. hydrochloric acid/ethanol (1:9 v/v, 0.71 ml) was hydrogenated over pre-reduced 10% palladium oxide on charcoal (80 mg, 50% aqueous paste) in absolute ethanol (5 ml). The mixture was filtered through hyflo and evaporated in vacuo to give an oil which was purified by FCC eluting with toluene-ethanol-triethylamine (95:5:1) to give the title compound as a white solid (0.22 g) m.p. 70°-71.5°.

Workup

  1. filtrationThe mixture was filtered through hyflo
  2. customevaporated in vacuo
  3. customto give an oil which
  4. customwas purified by FCC
  5. washeluting with toluene-ethanol-triethylamine (95:5:1)

Sources & evidence

ORD record
ord-530cd3997771471080f416dc13d175eb
Source dataset
uspto-grants-1990_09
Patent number
US04959381

Reaction notes

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