Triethylamine → HCID 23453182, compound

HRID 1277683Notes

Reaction equation

HRID 1277683 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:12][OH:13])[CH:8]([OH:9])[CH:7]([OH:10])[CH:6]([OH:11])[CH2:5][NH:4]1.C(N(CC)CC)C.[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)([O-:23])=[O:22]>CO.O>[N+:21]([C:24]1[CH:25]=[CH:26][C:27]([C:28]([NH:1][CH2:2][C:3]2([CH2:12][OH:13])[CH:8]([OH:9])[CH:7]([OH:10])[CH:6]([OH:11])[CH2:5][NH:4]2)=[O:29])=[CH:31][CH:32]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 20449507HCID 20449507, compound

Product 1

HCID 23453182HCID 23453182, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

5.4 g of 2-aminomethyl-2-hydroxymethyl-3,4,5-trihydroxypiperidine are dissolved in 50 ml of a methanol/water mixture (1:1), and 3.92 ml of triethylamine and, at -5° C., 5.44 g of 4-nitrobenzoyl chloride are added. The mixture is stirred for 24 hours and evaporated in vacuo, the residue is taken up in ether/water and the phases are separated. The aqueous phase is extracted once with ether and the product phase is then evaporated. The residue is dissolved in a little water and the solution is discharged onto a column 120 cm long and 4 cm wide which contains cellulose as the stationary phase and 99% pure acetone as the mobile phase. The column is eluted successively with 99% pure acetone, 95% pure acetone and finally 90% pure acetone. The individual fractions are examined by thin layer chromatography to determine their content of the required compound. The fractions containing the desired product are collected and evaporated. 2.6 g of 2-(4-nitrobenzoylaminomethyl)-2-hydroxymethyl-3,4,5 -trihydroxypiperidine are obtained.

Workup

  1. customevaporated in vacuo
  2. customthe phases are separated
  3. extractionThe aqueous phase is extracted once with ether
  4. customthe product phase is then evaporated
  5. dissolutionThe residue is dissolved in a little water
  6. washThe column is eluted successively with 99% pure acetone, 95% pure acetone and finally 90% pure acetone
  7. additionThe fractions containing the desired product
  8. customare collected
  9. customevaporated

Sources & evidence

ORD record
ord-695578e2a7b84a9aabca4ea5b7f890b7
Source dataset
uspto-grants-1981_07
Patent number
US04278683

Reaction notes

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