Benzocaine → HCID 22105618, compound

HRID 1455963Notes

Reaction equation

HRID 1455963 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH:15]=O)=[N:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)[CH3:18]>>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][NH:27][C:24]2[CH:23]=[CH:22][C:21]([C:20]([O:19][CH2:17][CH3:18])=[O:28])=[CH:26][CH:25]=2)=[N:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 2337BenzocaineHCID 22105558HCID 22105558, compound

Product 1

HCID 22105618HCID 22105618, compound

Conditions

Temperature
120 °C

Procedure

2-Benzyloxypyrazine-3-aldehyde (455 mg) was mixed with ethyl-4-aminobenzoate (321 mg) and stirred at 120° C. for 1 hour. The solid was then azeotroped with toluene (20 mL) to remove the last traces of water. The residue was dissolved in ethanol (10 mL) under argon, and sodium borohydride (81 mg) added with stirring at ambient temperature. The mixture was then heated to reflux for one hour, and allowed to cool to ambient temperature over 16 hours. Water (70 mL) was added, and the mixture acidified to pH 3 with acetic acid and then extracted with ethyl acetate (4×10 mL), washed with water (50 mL), brine (50 mL) and dried over magnesium sulphate. The residue was purified by MPLC (3% ethyl acetate in dichloromethane, silica) to give ethyl 4-[2-benzyloxypyrazin-3-ylmethylamino]benzoate yield, 460 mg, mp 111.7° C.

Workup

  1. customThe solid was then azeotroped with toluene (20 mL)
  2. customto remove the last traces of water
  3. dissolutionThe residue was dissolved in ethanol (10 mL) under argon
  4. additionsodium borohydride (81 mg) added
  5. stirringwith stirring at ambient temperature
  6. temperatureThe mixture was then heated
  7. temperatureto reflux for one hour
  8. temperatureto cool to ambient temperature over 16 hours
  9. additionWater (70 mL) was added
  10. extractionextracted with ethyl acetate (4×10 mL)
  11. washwashed with water (50 mL), brine (50 mL)
  12. dry with materialdried over magnesium sulphate
  13. customThe residue was purified by MPLC (3% ethyl acetate in dichloromethane, silica)

Sources & evidence

ORD record
ord-f14798245add40c084f81810dbd4d56c
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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