HCID 67578953, compound → HCID 67578508, compound

HRID 361722Notes

Reaction equation

HRID 361722 reaction equation
[BrH:1].[CH:2]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH:17]=[CH2:18])([CH3:4])[CH3:3]>C(O)C.[Pd]>[BrH:1].[CH:2]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][CH3:18])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 67578953HCID 67578953, compound

Product 1

HCID 67578508HCID 67578508, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-isopropyl-3-(2-allylphenoxy)propylamine hydrobromide (313 mg) in ethanol was hydrogenated at ambient temperature and pressure for 3 hours using a catalyst of palladium on carbon (10% w/w, 30 mg). The catalyst was removed by filtration and the filtrate evaporated to give a solid which was crystallised from a mixture of propan-2-ol and diethyl ether to give N-isopropyl-3-(2-propylphenoxy)propylamine hydrogen bromide as a colourless solid (204 mg), m.p. 89°-90°; microanalysis, found: C, 56.6; H, 8.2; N, 4.43%; C15H25NO.HBr requires: C,57.0; H, 8.3; N, 4.70%; NMR([CD3 ]2SO): 0.92(3H,t), 1.25(6H,d), 1.55(2H,m), 2.10(2H,m), 2.51(2H,m), 3.10(2H,t), 3.31(1H,m), 4.05(2H,t), 6.90(2H,m), 7.13(1H,m) and 8.46(2H,m); m/z 236(M+H).

Workup

  1. customwas hydrogenated at ambient temperature
  2. customThe catalyst was removed by filtration
  3. customthe filtrate evaporated
  4. customto give a solid which
  5. customwas crystallised from a mixture of propan-2-ol and diethyl ether

Sources & evidence

ORD record
ord-c8bd05d0b6864042a25d22e1d2a6812c
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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