Hydrochloric Acid → HCID 10247510, compound

HRID 728179Notes

Reaction equation

HRID 728179 reaction equation
[CH2:1]([NH:3][C:4]1[O:5][C:6]2[CH:12]=[C:11]([CH2:13][CH2:14][C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[CH:10]=[CH:9][C:7]=2[N:8]=1)[CH3:2].[CH2:20]=O.Cl.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(O)(=O)C>[CH2:1]([NH:3][C:4]1[O:5][C:6]2[CH:12]=[C:11]([CH2:13][CH2:14][C:15]3[O:16][C:17]([CH2:20][N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:18][CH:19]=3)[CH:10]=[CH:9][C:7]=2[N:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8082PiperidineHCID 10467596HCID 10467596, compound

Product 1

HCID 10247510HCID 10247510, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-ethylamino-6-[2-(2-furyl)ethyl]benzoxazole (0.93 g), 37% formalin (0.30 ml), concentrated hydrochloric acid (0.35 ml) and piperidine (0.34 g) in acetic acid (10 ml) was stirred at 70° C. for 2 hours. After the solvent was evaporated in vacuo, saturated aqueous sodium bicarbonate was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel by eluting with ethyl acetate-toluene (2:8, V/V). The free base was converted to the maleate in a usual way and recrystallized from a mixture of ethanol and diethyl ether to give 2-ethylamino-6-[2-(5-piperidinomethylfuran-2-yl)ethyl]benzoxazole 5/4 maleate (0.45 g).

Workup

  1. customAfter the solvent was evaporated in vacuo, saturated aqueous sodium bicarbonate
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washby eluting with ethyl acetate-toluene (2:8, V/V)
  9. customrecrystallized from a mixture of ethanol and diethyl ether

Sources & evidence

ORD record
ord-45d55703f0fd49d29754b91ff3e3c1c4
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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