Triethylamine → HCID 178469762, compound

HRID 1258040Notes

Reaction equation

HRID 1258040 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[N:10]=[CH:9][NH:8][CH:7]=1.Br[CH2:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15].CCN(CC)CC>CCO>[CH2:17]([O:16][C:14]([C:13]1[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH2:5][CH2:4][NH:3][CH:12]=1)=[O:15])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66144Ethyl bromopyruvateHCID 178478691HCID 178478691, compound

Product 1

HCID 178469762HCID 178469762, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of histamine dihydrochloride (5.52 g, 30 mmol), ethyl bromopyruvate (5.0 mL, 36 mmol), and active carbon (500 mg) in anhydrous EtOH (80 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, Et3N (30 mL) was added, and the mixture was refluxed at 90° C. for 6 hours. The active carbon was filtered off, and the filtrate was concentrated in vacuo. The residue was taken up in CHCl3, and washed twice with water, then dried over Na2SO4, and evaporated in vacuo. The residual oil was purified by column chromatography on silica gel eluting with hexane-EtOAc (60:40) to give the title compound as a pale-yellow solid. 1H-NMR (CDCl3): δ 7.49 (1H, d)), 7.00 (1H, s), 6.79 (1H, s), 4.85 (1H, br s), 4.30 (2H, q), 3.38 (2H, m), 3.06 (2H, m), 1.36 (3H, t); MS (ES): 208 (MH+).

Workup

  1. temperaturewas refluxed under nitrogen for 24 hours
  2. temperaturethe mixture was refluxed at 90° C. for 6 hours
  3. filtrationThe active carbon was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. washwashed twice with water
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo
  8. customThe residual oil was purified by column chromatography on silica gel eluting with hexane-EtOAc (60:40)

Sources & evidence

ORD record
ord-2da4af7ea8434836930a5cd5859a3214
Source dataset
uspto-grants-2013_06
Patent number
US08466143B2

Reaction notes

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