Sodium Hydroxide → HCID 53979715, compound

HRID 596852Notes

Reaction equation

HRID 596852 reaction equation
O=C1CNCCN1.[CH2:8]([N:10]([CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][NH:18][C:17](=O)[CH:16]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:11][CH3:12])[CH3:9].[OH-].[Na+].C1(C2NCCN(CCN(CC)CC)C2)C=CC=CC=1>O.CCOCC.O1CCOCC1>[CH2:8]([N:10]([CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH:16]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:11][CH3:12])[CH3:9]

Participants

8

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 231360Piperazin-2-oneHCID 53877629HCID 53877629, compoundHCID 54011008HCID 54011008, compound

Product 1

HCID 53979715HCID 53979715, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

89 g. of said keto piperazine dissolved in 200 cc. of dioxane are added drop by drop to a suspension of 20 g. of lithium aluminum hydride LiAlH4 in 800 cc. of ether. After addition of the keto piperazine, the reaction mixture is boiled under reflux for 6 hours. It is then decomposed by successively adding 20 cc. of 15% sodium hydroxide, 20 cc. of water, 60 cc. of 15% sodium hydroxide solution, and finally 40 cc. of water. The filtered solution is concentrated by evaporation and the residue is distilled in a vacuum. The resulting oil which distills at a temperature between 102° C. and 115° C./0.05 mm. Hg, is dissolved in benzene and is extracted therefrom by shaking in 10 % hydrochloric acid. The base is set free from its hydrochloride solution by the addition of 10 % sodium hydroxide solution and is repeatedly distilled in a vacuum. An almost colorless oil of the boiling point 114°-117° C./0.07 mm. Hg is obtained. The yield corresponds to the theoretical yield. The compound contains a small amount of 3-phenyl-1-(diethylamino ethyl) piperazine.

Workup

  1. additionto a suspension of 20 g
  2. temperatureunder reflux for 6 hours
  3. additionby successively adding 20 cc
  4. concentrationThe filtered solution is concentrated by evaporation
  5. distillationthe residue is distilled in a vacuum
  6. distillationThe resulting oil which distills at a temperature between 102° C. and 115° C./0.05 mm. Hg
  7. dissolutionis dissolved in benzene
  8. extractionis extracted
  9. additionThe base is set free from its hydrochloride solution by the addition of 10 % sodium hydroxide solution
  10. distillationis repeatedly distilled in a vacuum
  11. customAn almost colorless oil of the boiling point 114°-117° C./0.07 mm. Hg is obtained

Sources & evidence

ORD record
ord-f71448c2ae3443c5a2f14e74d26c6c6a
Source dataset
uspto-grants-1977_03
Patent number
US04012389

Reaction notes

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