Hydrochloric Acid → HCID 67578950, compound

HRID 361718Notes

Reaction equation

HRID 361718 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:10]([NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=1)([CH3:12])[CH3:11].[ClH:25]>C(O)C.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[ClH:25].[CH:10]([NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:19]=1)([CH3:12])[CH3:11]

Participants

9

Reactant 3

HCID 313Hydrochloric AcidHCID 66827Phenylboronic AcidHCID 29015667HCID 29015667, compound

Product 1

HCID 67578950HCID 67578950, compound

Reagents, catalysts & solvents 5

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of phenyl boronic acid (0.36 g) in ethanol (3.0 ml) was added to a stirred suspension of N-isopropyl-3-(3-bromophenoxy)propylamine (1.0 gm) and tetrakis(triphenylphosphine)-palladium (100 mg) in aqueous 2M sodium carbonate (4.0 ml) and toluene (6.5 ml) under an atmosphere of argon. The mixture was heated at reflux for 18 hours and then cooled to ambient temperature. The reaction mixture was diluted with ethyl acetate, washed with aqueous 2M sodium hydroxide and the organic phase was evaporated to give a solid. The solid was dissolved in hot ethanol, the solution was filtered, and the filtrate evaporated to give a residue which was purified by dry-flash column chromatography on silica gel (Merck 60H, Art No 7736) using ethyl acetate initially followed by ethyl acetate/1% triethylamine as eluent. There was thus obtained an oil which was treated with ethereal hydrogen chloride to give a solid which was recrystallised from isopropyl alcohol to give N-isopropyl-3-(3-phenylphenoxy)propylamine hydrogen chloride (0.26 g) as a solid, m.p. 147°-149° C.; microanalysis, found: C, 70.7; H, 7.9; N, 4.7; Cl, 11.5%; C18H23NO. HCl requires: C, 70.7; H, 7.91; N, 4.58; Cl, 11.6%; NMR(CD3 !2SO): 1.27(6H,d), 2.16(2H,m), 3.05(2H,br.m), 3.30(1H,m), 4.18(2H,t), 6.96(1H,d of d), 7.24(2H,d of d), 7.31-7.52(4H,m), 7.67(2H,d of d) and 9.07(1H,br.s); m/z 270(M+H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hours
  3. washwashed with aqueous 2M sodium hydroxide
  4. customthe organic phase was evaporated
  5. customto give a solid
  6. filtrationthe solution was filtered
  7. customthe filtrate evaporated
  8. customto give a residue which
  9. customwas purified by dry-flash column chromatography on silica gel (Merck 60H, Art No 7736)
  10. customThere was thus obtained an oil which
  11. customto give a solid which
  12. customwas recrystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-e020d96d33b24693ab0660e9980f9819
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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