Hydrochloric Acid → HCID 86753655, compound

HRID 361719Notes

Reaction equation

HRID 361719 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[CH:11]([NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=1)([CH3:13])[CH3:12].[ClH:26]>C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC.C(OCC)(=O)C>[ClH:26].[CH:11]([NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[CH:21][CH:20]=1)([CH3:13])[CH3:12]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 27332672-Methylphenyl boronic acidHCID 29015593HCID 29015593, compound

Product 1

HCID 86753655HCID 86753655, compound

Reagents, catalysts & solvents 3

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

2-Methylphenyl boronic acid (0.42 g) was added to a solution of N-isopropyl-3-(4-bromophenoxy)propylamine (1.0 g) and tetrakis triphenylphosphine palladium (100 mg) in aqueous 2M sodium carbonate (8.4 ml) and dimethoxyethane (5 ml). The mixture was heated at 80° C. for 18 hours, cooled to ambient temperature and diluted with ethyl acetate. The reaction mixture was washed with dilute sodium hydroxide solution, brine, dried (MgSO4) and evaporated. The residue was purified by dry flash column chromatography on silica gel (Merck 60H, Art No 7736) using a 5:95 v/v mixture of methanol and dichloromethane to give an oil. This oil was treated with ethereal hydrogen chloride to give a solid which was recrystallised from isopropyl alcohol to give N-isopropyl-3-[4-(2-methylphenyl)phenoxy]propylamine hydrogen chloride (0.38 g) as a solid, m.p. 157°-158° C.; microanalysis, found: C, 71.6; Hi 8.2; N, 4.4; Cl, 10.8%; C19H25NO. HCl requires: C, 71.3; H, 8.19; N, 4.38; Cl, 11.1%; NMR([CD3 ]2SO): 1.27(6H,d), 2.14(2H,m), 2.22(3H,s), 3.05(2H,t), 3.29(1H,m), 4.13(2H,t), 7.01(2H,d) and 7.12-7.30(6H,m); m/z 284(M+H).

Workup

  1. temperaturecooled to ambient temperature
  2. washThe reaction mixture was washed with dilute sodium hydroxide solution, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified
  6. customby dry flash column chromatography on silica gel (Merck 60H, Art No 7736)
  7. additiona 5:95 v/v mixture of methanol and dichloromethane
  8. customto give an oil
  9. customto give a solid which
  10. customwas recrystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-ff69a1b2d0594b8784b7c312d0784d3f
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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