Hexane → 4-Amino-3-chloro-alpha-[[[6-(2-pyridinylethoxy)hexyl]amino]methyl]-5-(trifluoromethyl)benzenemethanol

HRID 1032709Notes

Reaction equation

HRID 1032709 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](CC2C=CC=CC=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[OH:13])=[CH:4][C:3]=1[Cl:38].CCCCCC>C(O)C.Cl.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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[OH:13])=[CH:4][C:3]=1[Cl:38]

Participants

6

Reactant 2

HCID 8058HexaneHCID 221649134-Amino-3-chloro-alpha-[[(phenylmethyl)[6-(2-pyridinylethoxy)hexyl]amino]methyl]-5-(trifluoromethyl)benzenemethanol

Product 1

HCID 221649174-Amino-3-chloro-alpha-[[[6-(2-pyridinylethoxy)hexyl]amino]methyl]-5-(trifluoromethyl)benzenemethanolYield 69.4%

Reagents, catalysts & solvents 3

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent2×HCID 21887872Ethanol hydrochlorideSolvent

Procedure

A solution of 4-amino-3-chloro-α-[[(phenylmethyl)[6-(2-pyridinylethoxy)hexyl]amino]methyl]-5-(trifluoromethyl)benzenemethanol (1.50 g) in absolute ethanol (10 ml) and conc. hydrochloric acid/ethanol (1:9 v/v, 2.48 ml) was hydrogenated over pre-reduced 10% palladium oxide on charcoal (50% aqueous, 300 mg) in absolute ethanol (10 ml). The mixture was filtered through hyflo and evaporated in vacuo to give an oil. Purification by FCC eluting with toluene-ethanol- triethylamine (95:5:1) gave a pink oil. Trituration with hexane afforded the title compound as a pale orange solid (0.87 g), m.p. 51.5°-53°.

Workup

  1. filtrationThe mixture was filtered through hyflo
  2. customevaporated in vacuo
  3. customto give an oil
  4. customPurification by FCC
  5. washeluting with toluene-ethanol- triethylamine (95:5:1)
  6. customgave a pink oil

Sources & evidence

ORD record
ord-903c62c25da141a7bd756f4148c7e3ed
Source dataset
uspto-grants-1990_09
Patent number
US04959381

Reaction notes

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