Phosphoric Acid → HCID 5008364, compound

HRID 853791Notes

Reaction equation

HRID 853791 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.[CH3:12][C:13]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:14]=1[CH:15]=O.P(=O)(O)(O)O>O>[CH3:12][C:13]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:14]=1[CH:15]1[C:6]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:9][CH2:10][NH:11]1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 618142,4-DimethylbenzaldehydeHCID 748663-Methoxyphenethylamine

Product 1

HCID 5008364HCID 5008364, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
37 °C

Procedure

3-Methoxyphenylethylamine (1.51 g) and 2,4-dimethylbenzaldehyde (1.34 g) were mixed together. Phosphoric acid, 85%, (20 mL) was added then the reaction was warmed to 37° C. for 60 h. The reaction was cooled, poured into water (300 mL) then washed with diethyl ether (2×50 mL). The aqueous layer was diluted to 700 mL with water, made basic (pH=10) by the slow addition of sodium hydroxide, and then extracted with diethyl ether (2×150 mL). The organic extracts were dried and evaporated. The resulting residue was purified by silica gel chromatography (eluant: ethyl acetate-hexane, gradient from 1:1 to 100% ethyl acetate) to give the title compound (1.458 g). MS: 268.2 (MH+); HPLC tR: 1.71 min (method D); TLC Rf: 0.21 (ethyl acetate); 1H NMR (DMSO-d6): 6.96 (s, 1H), 6.86 (s, 2H), 6.67 (d, 1H, J=2.3 Hz), 6.59 (dd, 1H, J=2.5, 8.5 Hz), 6.44 (d, 1H, J=8.5 Hz), 5.07 (s, 1H), 3.69 (s, 3H), 3.03-3.11 (m, 1H), 2.82-2.89 (m, 2H), 2.63-2.77 (m, 1H), 2.26 (s, 3H), 2.23 (s, 3H).

Workup

  1. temperatureThe reaction was cooled
  2. washthen washed with diethyl ether (2×50 mL)
  3. additionThe aqueous layer was diluted to 700 mL with water
  4. additionby the slow addition of sodium hydroxide
  5. extractionextracted with diethyl ether (2×150 mL)
  6. customThe organic extracts were dried
  7. customevaporated
  8. customThe resulting residue was purified by silica gel chromatography (eluant: ethyl acetate-hexane, gradient from 1:1 to 100% ethyl acetate)

Sources & evidence

ORD record
ord-1882d10198fd41499b4281b931997325
Source dataset
uspto-grants-2007_08
Patent number
US07256201B2

Reaction notes

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