Pyridine → HCID 21388469, compound

HRID 1834068Notes

Reaction equation

HRID 1834068 reaction equation
C(C(N1CCNCC1)C1C=CC([O:10]C)=C(OC)C=1)#N.N1C=CC=CC=1.N1(C(C[Cl:34])=O)CCCC1.[C:35]([CH:37]([N:48]1[CH2:53][CH2:52][N:51]([CH2:54][C:55]([N:57]2[CH2:61][CH2:60][CH2:59][CH2:58]2)=[O:56])[CH2:50][CH2:49]1)[C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([O:46][CH3:47])[CH:39]=1)#[N:36]>C1C=CC=CC=1>[OH2:10].[ClH:34].[C:35]([CH:37]([N:48]1[CH2:49][CH2:50][N:51]([CH2:54][C:55]([N:57]2[CH2:58][CH2:59][CH2:60][CH2:61]2)=[O:56])[CH2:52][CH2:53]1)[C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([O:46][CH3:47])[CH:39]=1)#[N:36]

Participants

6

Reactant 4

HCID 1049PyridineHCID 884401-(Chloroacetyl)pyrrolidineHCID 21388458HCID 21388458, compoundHCID 21388459HCID 21388459, compound

Product 1

HCID 21388469HCID 21388469, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

To 17.7 g. of N-(α-cyano-3,4-dimethoxybenzyl)piperazine was added 60 ml. of benzene and then 5.3 g. of pyridine. To the resulting solution was added dropwise 7.9 g. of pyrrolidylcarbonylmethyl chloride dissolved in 20 ml. of benzene over a period of about 10 minutes with stirring at room temperature. After dropping, the temperature was raised slowly and the mixture to separate benzene layer which was washed with water and dried over sodium sulfate. The solvent was distilled off to give 15 g. of N-(α-cyano-3,4-dimethoxybenzyl)-N'-pyrrolidinocarbonylmethylpiperazine as an oily substance. This product was dissolved in benzene and the resultant solution was saturated with dry hydrochloric gas to separate crystal which was collected by filtration. Recrystrallization from iso-propanol afforded N-(α-cyano-3,4-dimethoxybenzyl)-N'-pyrrolidinocarbonylmethylpiperazine hydrochloride monohydrate having a melting point of 155° to 157° C.

Workup

  1. additionTo the resulting solution was added dropwise 7.9 g
  2. temperaturethe temperature was raised slowly
  3. customthe mixture to separate benzene layer which
  4. washwas washed with water
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled off
  7. customto give 15 g
  8. customwith dry hydrochloric gas
  9. customto separate crystal which
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-1386b6dc03884f6c92338685412027d2
Source dataset
uspto-grants-1978_01
Patent number
US04068070

Reaction notes

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