4-Methylpiperidine → HCID 101872261, compound

HRID 1415409Notes

Reaction equation

HRID 1415409 reaction equation
[CH3:1][C:2]1[C:7]2[O:8][C@:9]3([CH3:49])[O:12][CH:13]=[CH:14][C@H:15]([O:47][CH3:48])[C@@H:16]([CH3:46])[C@@H:17]([O:42][C:43]([CH3:45])=[O:44])[C@H:18]([CH3:41])[C@H:19]([OH:40])[C@H:20]([CH3:39])[C@@H:21]([OH:38])[C@@H:22]([CH3:37])[CH:23]=[CH:24][CH:25]=[C:26]([CH3:36])[C:27]([NH:29][C:30]4[C:34](=[O:35])[C:4](=[C:5]([C:32](=[O:33])[CH:31]=4)[C:6]=2[C:10]3=[O:11])[C:3]=1[OH:50])=[O:28].[CH3:51][CH:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1>O1CCOCC1.O>[CH3:37][C@@H:22]1[C@H:21]([OH:38])[C@@H:20]([CH3:39])[C@@H:19]([OH:40])[C@@H:18]([CH3:41])[C@H:17]([O:42][C:43]([CH3:45])=[O:44])[C@H:16]([CH3:46])[C@@H:15]([O:47][CH3:48])[CH:14]=[CH:13][O:12][C@:9]2([CH3:49])[C:10](=[O:11])[C:6]3=[C:7]([O:8]2)[C:2]([CH3:1])=[C:3]([OH:50])[C:4]2=[C:5]3[C:32]([OH:33])=[C:31]([N:55]3[CH2:56][CH2:57][CH:52]([CH3:51])[CH2:53][CH2:54]3)[C:30](=[C:34]2[OH:35])[NH:29][C:27](=[O:28])[C:26]([CH3:36])=[CH:25][CH:24]=[CH:23]1

Participants

5

Reactant 2

HCID 693814-MethylpiperidineHCID 6436726Rifamycin S

Product 1

HCID 101872261HCID 101872261, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 25 g (0.036 mol) of rifamycin S in 50 ml of dioxane is mixed with 20 ml (0.2 mol) of 4-methylpiperidine and left to stand at 20° C until the reaction mixture, which is initially deep violet in colour has assumed an orange-yellow colour. The reaction mixture is now diluted with water, acidified to pH 5 and extracted with chloroform. After drying and evaporating the chloroform extract, the evaporation residue is dissolved in methanol and mixed dropwise with concentrated ascorbic acid solution. After standing for some time yellow crystals separate out and are filtered off and twice recrystallised from 80 % strength aqueous methanol. 3-(4-methylpiperidino)-rifamycin SV is thus obtained in crystals of melting point 185°-186° C.

Workup

  1. waitleft
  2. customto stand at 20° C until the reaction mixture, which
  3. extractionextracted with chloroform
  4. customAfter drying
  5. customevaporating the chloroform
  6. extractionextract
  7. dissolutionthe evaporation residue is dissolved in methanol
  8. additionmixed dropwise with concentrated ascorbic acid solution
  9. customseparate out
  10. filtrationare filtered off
  11. customtwice recrystallised from 80 % strength aqueous methanol

Sources & evidence

ORD record
ord-7443fe8fa2c543a0adc91910d562408d
Source dataset
uspto-grants-1977_01
Patent number
US04005077

Reaction notes

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