Benzoyl chloride → HCID 23453190, compound

HRID 1277682Notes

Reaction equation

HRID 1277682 reaction equation
NC[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:16](CC)CC)C.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO.O>[C:21]([NH:16][C:3]1([CH2:12][OH:13])[CH:8]([OH:9])[CH:7]([OH:10])[CH:6]([OH:11])[CH2:5][NH:4]1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 20449507HCID 20449507, compound

Product 1

HCID 23453190HCID 23453190, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
-10 °C

Procedure

2.0 g of 2-aminomethyl-2-hydroxymethyl-3,4,5-trihydroxypiperidine are dissolved in 20 ml of methanol/water (1:1), 1.45 ml of triethylamine are added and the mixture is cooled to -10° C. After adding 1.635 g of benzoyl chloride, the mixture is stirred at -10° C. for 30 minutes and then at room temperature for 20 hours. The solution is evaporated in vacuo and the residue is taken up in 40 ml of methanol/water (2:1). This solution is discharged onto a column 40 cm long and 3 cm wide which is filled with a cation exchanger in the H+ form. The column is first washed with 1 l of a methanol/water mixture (2:1) and is then eluted with 0.1% strength ammonia in methanol/water (2:1). 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. The residue is dissolved in a little methanol and the solution is left to stand, whereupon crystallisation soon starts. The mixture is diluted with a little isopropanol and the crystals are filtered off and washed with isopropanol and diethyl ether. 0.8 g of 2-benzoylamino-2-hydroxymethyl-3,4,5-trihydroxypiperidine of melting point 154° to 156° C. is obtained.

Workup

  1. waitat room temperature for 20 hours
  2. customThe solution is evaporated in vacuo
  3. addition3 cm wide which is filled with a cation exchanger in the H+ form
  4. washThe column is first washed with 1 l of a methanol/water mixture (2:1)
  5. washis then eluted with 0.1% strength ammonia in methanol/water (2:1)
  6. additionThe fractions containing the desired product
  7. customare collected
  8. customevaporated
  9. dissolutionThe residue is dissolved in a little methanol
  10. waitthe solution is left
  11. customto stand, whereupon crystallisation
  12. additionThe mixture is diluted with a little isopropanol
  13. filtrationthe crystals are filtered off
  14. washwashed with isopropanol and diethyl ether

Sources & evidence

ORD record
ord-0dfc1a2886654b039c8fab53b70cff1a
Source dataset
uspto-grants-1981_07
Patent number
US04278683

Reaction notes

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