Hydrochloric Acid → HCID 24788264, compound

HRID 733299Notes

Reaction equation

HRID 733299 reaction equation
C([CH:8]([NH2:32])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19](=[O:29])[CH2:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])=[CH:13][C:12]=1[O:30][CH3:31])(OC(C)(C)C)=O.[ClH:33].C(OCC)C>O1CCOCC1>[ClH:33].[NH2:32][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19](=[O:29])[CH2:20][C:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:22])=[CH:13][C:12]=1[O:30][CH3:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68819001HCID 68819001, compound

Product 1

HCID 24788264HCID 24788264, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 5-(4-(2-boc-aminoethoxy)-3-methoxyphenyl)-1-phenylpentane-1,3-dione (211 mg, 0.48 mmol) dissolved in dioxane (5 ml) was added drop wise dry HCl in dioxane (4 M, 0.36 ml, 1.43 mmol) and stirred at RT for 1 h. After this time diethyl ether (20 ml) was added and an off-white emulsion was visible. The solvents were removed by evaporation in vacuo to give a brown gum residue. Residual dioxane was removed by azeotroping with methanol and then drying the product on high pressure line to give 5-(4-(2-aminoethoxy)-3-methoxyphenyl)-1-phenylpentane-1,3-dione hydrochloride (163 mg, 99%) as a brown powdery solid: mp 80° C.; LCMS 342 [M+H]+, 364 [M+Na]+, 1H NMR (400 MHz, MeOD) δ 2.79-2.82 (2H, m, CH2), 2.99-3.02 (2H, m, CH2), 3.33-3.34 (2H, m, NHCH2+solvent signal), 3.90 (3H, s, OCH3), 4.20 (2H, t, J=5.0 Hz, NHCH2CH2), 6.37 (1H, s, enol CH), 6.84-6.98 (3H, m, 3×ArH), 7.48-7.60 (3H, m, 3×ArH), 7.93 (2H, d, J=8.0 Hz, 2×ArH) ppm; 13C NMR (100 MHz, MeOD) δ 33.04, 41.40, 41.83, 57.31, 68.16, 98.35, 114.54, 117.51, 122.73, 128.84 (2×CH), 130.58 (2×CH), 134.34, 136.75, 137.93, 147.75, 151.73, 184.57, 198.44 ppm.

Workup

  1. customThe solvents were removed by evaporation in vacuo
  2. customto give a brown gum residue
  3. customResidual dioxane was removed
  4. customby azeotroping with methanol
  5. customdrying the product on high pressure line

Sources & evidence

ORD record
ord-194b66894d2d4e27b6524d73bfc101a2
Source dataset
uspto-grants-2009_09
Patent number
US07589123B2

Reaction notes

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