Water → HCID 21454978, compound

HRID 436014Notes

Reaction equation

HRID 436014 reaction equation
ClC1CNC(C2NC(=O)C(C3CCC(Cl)CN3)NC2=O)CC1.O.Cl.Cl.[OH:26][CH:27]1[CH2:32][NH:31][CH:30]([CH:33]2[NH:38][C:37](=[O:39])[CH:36]([CH:40]3[CH2:45][CH2:44][CH:43]([OH:46])[CH2:42][NH:41]3)[NH:35][C:34]2=[O:47])[CH2:29][CH2:28]1>CO>[OH:46][CH:43]1[CH2:42][NH:41][CH:40]([CH:36]2[NH:35][C:34](=[O:47])[CH:33]([CH:30]3[CH2:29][CH2:28][CH:27]([OH:26])[CH2:32][NH:31]3)[NH:38][C:37]2=[O:39])[CH2:45][CH2:44]1

Participants

5

Reactant 3

HCID 962WaterHCID 1147283,6-Bis(5-chloro-2-piperidyl)-2,5-piperazinedioneHCID 21454977HCID 21454977, compound

Product 1

HCID 21454978HCID 21454978, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.0 G. of 3,6-bis(5-chloro-2-piperidinyl)-2,5-piperazinedione is heated in 50 ml. of water for 1/2 hour on a steam bath. The solution is filtered, neutralized with dilute sodium hydroxide and freeze-dried to a white solid weighing 1.16 g. Purification of 300 mg. is accomplished by chromatography on 6 × 1000 μ on silica gel plate using 5:1:2 n-butanol:acetic acid:water as an eluant to give 165 mg. which is dissolved in 15 ml. of hot methanol. Filter solution and bubble in hydrogen chloride gas. Collect precipitate and wash 2 × 5 ml. with methanol and 20 ml. of ether to give 80 mg. of 3,6-bis-(5-hydroxy-2-piperidinyl)-2,5-piperazinedione dihydrochloride.

Workup

  1. filtrationThe solution is filtered
  2. customfreeze-dried to a white solid
  3. customPurification of 300 mg
  4. customacetic acid:water as an eluant to give 165 mg
  5. dissolutionwhich is dissolved in 15 ml
  6. customFilter solution and bubble in hydrogen chloride gas
  7. customCollect precipitate
  8. washwash 2 × 5 ml
  9. customof ether to give 80 mg

Sources & evidence

ORD record
ord-e26d0b6fb67f4a35b03d50ccd0a8a3ed
Source dataset
uspto-grants-1977_02
Patent number
US04007190

Reaction notes

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