Hydrochloric Acid → HCID 53899394, compound

HRID 361714Notes

Reaction equation

HRID 361714 reaction equation
[CH:1]([NH:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][C:10]=1[CH2:20][CH:21]=[CH2:22])([CH3:3])[CH3:2].Cl>C(O)C.[Pd].CCOCC>[CH:1]([NH:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][C:10]=1[CH2:20][CH2:21][CH3:22])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 10780929HCID 10780929, compound

Product 1

HCID 53899394HCID 53899394, compoundYield 66.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of N-isopropyl-3-(2-allyl-4-butoxy-phenoxy)propylamine (404 mg) in ethanol (15 ml) was hydrogenated at ambient temperature and pressure for 8 hours using a catalyst of palladium on carbon (10% w/w, 80 mg). The catalyst was removed by filtration and the filtrate evaporated to give a yellow oil. The oil was purified by flash column chromatography on silica gel (Merck Art No 9385) using a 70:30:1 mixture of ethyl acetate, hexane and triethylamine to give an oil. The oil was dissolved in ether and excess ethereal hydrogen chloride was added until crystallisation began. The solid was collected by filtration and recrystallised from ethyl acetate to give N-isopropyl-3-(4-butoxy-2-propylphenoxy)propylamine (271 mg) as a white solid, m.p. 102 103° C.; microanalysis, found: C, 65.7; H, 10.2; N, 4.0%; C19H34NO2Cl. 0.25H2O requires: C, 65.5; H, 9.98; N, 4.02%; NMR ([CD3 ]2SO): 0.90(6H,m), 1.28(6H,d), 1.52(6H,m), 2.12(2H,m), 2.5(2H,m), 3.04(2H,m), 3.3(1H,m), 3.88(2H,t), 4.0(2H,t), 6.7(2H,t) and 6.85(1H,d); m/z 308 (M+H).

Workup

  1. customwas hydrogenated at ambient temperature
  2. customThe catalyst was removed by filtration
  3. customthe filtrate evaporated
  4. customto give a yellow oil
  5. customThe oil was purified by flash column chromatography on silica gel (Merck Art No 9385)
  6. additiona 70:30:1 mixture of ethyl acetate, hexane and triethylamine
  7. customto give an oil
  8. filtrationThe solid was collected by filtration
  9. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-c2cf0001d0cb4c33afa99fec618b2896
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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