Sodium Hydroxide → HCID 13049055, compound

HRID 839715Notes

Reaction equation

HRID 839715 reaction equation
[N+]([NH:4][C:5]([NH2:7])=[O:6])([O-])=O.[N:8]1([CH2:14][CH2:15][O:16][CH:17]2[CH2:21][CH2:20]N[CH2:18]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[OH-].[Na+]>C(O)C>[N:8]1([CH2:14][CH2:15][O:16][CH:17]2[CH2:21][CH2:20][N:4]([C:5]([NH2:7])=[O:6])[CH2:18]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 62372NitroureaHCID 2133316470001-70-6

Product 1

HCID 13049055HCID 13049055, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Nitrourea (7.3 g., 0.055 mole of 80% wet reagent) and 3-(2-piperidinoethoxy)pyrrolidine were stirred together in 100 ml. ethanol at reflux for 2 hr. After cooling, the reaction mixture was filtered and the filtrate concentrated to give 12.5 g. solid material which was determined by nuclear magnetic resonance spectrum analysis to be a salt. The crude product was treated with dilute sodium hydroxide solution and the free base extracted into chloroform twice. The chloroform extracts were combined, washed with water, dried over magnesium sulfate, filtered, and concentrated to give 6.8 g. of off-white solid product. Recrystallization from isopropyl ether-isopropanol gave 3.7 g. (30.7%) white solid, m.p. 133.5°-135.5° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate concentrated
  4. customto give 12.5 g
  5. extractionthe free base extracted into chloroform twice
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give 6.8 g
  11. customRecrystallization from isopropyl ether-isopropanol
  12. customgave 3.7 g

Sources & evidence

ORD record
ord-321da87f42454aa680f9bdece59a0f9b
Source dataset
uspto-grants-1978_06
Patent number
US04096331

Reaction notes

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