Isopropanol → HCID 67826703, compound

HRID 361721Notes

Reaction equation

HRID 361721 reaction equation
[ClH:1].C([O:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][N:21]([CH3:25])[CH:22]([CH3:24])[CH3:23])=[CH:13][CH:12]=1)C1C=CC=CC=1.C(O)(C)C>[Pd].C(O)C>[ClH:1].[CH3:25][N:21]([CH2:20][CH2:19][CH2:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]([OH:26])=[O:9])=[CH:16][CH:15]=1)[CH:22]([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 86753657HCID 86753657, compound

Product 1

HCID 67826703HCID 67826703, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl-4-[3-(N-methyl-N-isopropylamino)-propoxy]benzoate hydrogen chloride (300 mg), isopropyl alcohol (20 ml) and a catalyst of palladium on carbon (10% w/w, 30 mg) was hydrogenated at ambient temperature and pressure for 16 hours. Ethanol was then added to dissolve precipitated product and the mixture was then filtered to remove inorganic material. The filtrate was evaporated to give 4-[3-(N-methyl-N-isopropylamino)propoxy]benzoic acid hydrogen chloride as a solid (172 mg), m.p. 167.8° C.; microanalysis, found: C, 56.2; H, 7.40; H, 4.70; N, 4.70%, C14H21NO3. HCl 0.6H2O requires C, 56.3; H, 7.87; N, 4.63%; NMR([CD3 ]2SO): 1.2-1.35(6H,q), 2.1-2.4(2H,m), 2.6-2.7(3H,d), 3.0-3.65(3H,m), 4.1-4.2(2H,t). 7.0-7.1(2H,d), 7.85-7.95(2H,d) and 10.5-10.8(1H, br s); m/z 252 (M+H).

Workup

  1. customwas hydrogenated at ambient temperature
  2. dissolutionto dissolve
  3. customprecipitated product
  4. filtrationthe mixture was then filtered
  5. customto remove inorganic material
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-4ec9020262ad488cbf1cb26a53ce724f
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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