Ethanol → HCID 178461156, compound

HRID 745144Notes

Reaction equation

HRID 745144 reaction equation
[CH3:1][C@@H:2]1[C@@H:16]2[C:11](=[C:12]([OH:31])[C@:13]3([OH:30])[C:21](=[O:22])[C:20]([C:23]([NH2:25])=[O:24])=[C:19]([OH:26])[C@@H:18]([N:27]([CH3:29])[CH3:28])[C@@H:14]3[C@H:15]2[OH:17])[C:9](=[O:10])[C:8]2[C:7]([OH:32])=[CH:6][CH:5]=[CH:4][C:3]1=2.C1(C)C=CC([S:39]([O-:42])(=[O:41])=[O:40])=CC=1.C(N(CC)CC)C.C([OH:53])C>O>[CH3:1][C@@H:2]1[C@@H:16]2[C:11](=[C:12]([OH:31])[C@:13]3([OH:30])[C:21](=[O:22])[C:20]([C:23]([NH2:25])=[O:24])=[C:19]([OH:26])[C@@H:18]([N:27]([CH3:28])[CH3:29])[C@@H:14]3[C@H:15]2[OH:17])[C:9](=[O:10])[C:8]2[C:7]([OH:32])=[CH:6][CH:5]=[CH:4][C:3]1=2.[S:39]([O:22][C:21]1[C:20](=[CH:19][CH:18]=[CH:14][CH:13]=1)[C:23]([O-:24])=[O:53])([OH:42])(=[O:41])=[O:40]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 8471TriethylamineHCID 178461153HCID 178461153, compound

Product 1

HCID 178461156HCID 178461156, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Doxycycline p-toluenesulphonate (40.0 g) prepared according to the process above was suspended in a mixture of ethanol (72.0 ml) and water (24.0 ml), with stirring. A solution of triethylamine (9.04 ml) in ethanol (9.04 ml) was added, causing dissolution followed by crystallisation. After stirring for 20 minutes, ethanol (144 ml) was added and the mixture stirred for a further 1 hour 30 minutes. The crystals were filtered, washed with ethanol (25 ml), then with acetone (12.5 ml) and dried at 35° C. The product, doxycycline monohydrate, weighed 22.12 g and complied with the U.S. Pharmacopoeia monograph requirements. The mother liquors were diluted with an equal volume of water and 5-sulphosalicylic acid (2.0 g) was added. After stirring overnight, the deposited solid was filtered, washed with 66% aqueous methanol and then with acetone, dried at 35° C., and gave 1.53 g of doxycycline sulphosalicylate.

Workup

  1. dissolutiondissolution
  2. customfollowed by crystallisation
  3. stirringAfter stirring for 20 minutes
  4. additionethanol (144 ml) was added
  5. stirringthe mixture stirred for a further 1 hour 30 minutes
  6. filtrationThe crystals were filtered
  7. washwashed with ethanol (25 ml)
  8. dry with materialwith acetone (12.5 ml) and dried at 35° C
  9. additionThe mother liquors were diluted with an equal volume of water and 5-sulphosalicylic acid (2.0 g)
  10. additionwas added
  11. stirringAfter stirring overnight
  12. filtrationthe deposited solid was filtered
  13. washwashed with 66% aqueous methanol
  14. dry with materialwith acetone, dried at 35° C.

Sources & evidence

ORD record
ord-80e8ac736036456393909ad331683318
Source dataset
uspto-grants-1986_07
Patent number
US04597904

Reaction notes

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