3-Acetamidopiperidine → HCID 131735651, compound

HRID 530955Notes

Reaction equation

HRID 530955 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8](=[O:10])[CH3:9])[CH2:2]1.N1CCCC(NC(=O)C)C1.[C:21]([C:29]([C:44]([OH:46])=[O:45])([OH:43])[C:30]([C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([OH:34])[C:31]([OH:33])=[O:32])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO>[C:35]([C:30]([C:31]([OH:33])=[O:32])([OH:34])[C:29]([C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([OH:43])[C:44]([OH:46])=[O:45])(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8](=[O:10])[CH3:9])[CH2:2]1

Participants

5

Reactant 3

HCID 41697193-AcetamidopiperidineHCID 7175791HCID 7175791, compoundHCID 12362975HCID 12362975, compound

Product 1

HCID 131735651HCID 131735651, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(c)Preparation of (R)—N-piperidin-3-ylacetamide Dibenzyol tartarate salt: In a RBF charged 500 ml of Methanol, 50 gm of N-piperidin-3-ylacetamide & 138 gm of L (+)-Dibenzoyl tartaric acid. The reaction was maintained for about 90 mins at room temperature and then heated to reflux. The reaction mass was maintained for about an hour at reflux and then cooled and maintained at room temperature for about 12.0 hours. Then, the product was filtered and washed with 100 ml methanol. Again charged the obtained wet cake in 800 ml methanol, heated to reflux and maintained reaction mass for 1.0 hr to get a clear solution. Cooled the reaction mass to room temperature and maintained for 12.0 hrs. The product was filtered and washed with 100 ml methanol. The product was dried at about 45-50° C. under vacuum. Unwanted S-isomer NMT 1.5% Dry Wt-20. Gm.

Workup

  1. temperatureheated to reflux
  2. temperatureThe reaction mass was maintained for about an hour
  3. temperatureat reflux
  4. temperaturecooled
  5. temperaturemaintained at room temperature for about 12.0 hours
  6. filtrationThen, the product was filtered
  7. washwashed with 100 ml methanol
  8. additionAgain charged the obtained wet cake in 800 ml methanol
  9. temperatureheated
  10. temperatureto reflux
  11. temperaturemaintained
  12. customreaction mass for 1.0 hr
  13. customto get a clear solution
  14. temperatureCooled the reaction mass to room temperature
  15. temperaturemaintained for 12.0 hrs
  16. filtrationThe product was filtered
  17. washwashed with 100 ml methanol
  18. customThe product was dried at about 45-50° C. under vacuum
  19. customUnwanted S-isomer NMT 1.5% Dry Wt-20

Sources & evidence

ORD record
ord-6e45b9d26e444187a3c8d80cfad13703
Source dataset
uspto-grants-2016_05
Patent number
US09353114B2

Reaction notes

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