Pyridine → HCID 21388467, compound

HRID 1657780Notes

Reaction equation

HRID 1657780 reaction equation
[C:1]([CH:3]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[C:5]=1[O:14][CH3:15])#[N:2].N1C=CC=CC=1.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C(OCC)C>[C:1]([CH:3]([N:16]1[CH2:21][CH2:20][N:19]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:18][CH2:17]1)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[C:5]=1[O:14][CH3:15])#[N:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 21388464HCID 21388464, compound

Product 1

HCID 21388467HCID 21388467, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

14.5 g. of N-(α-cyano-2,3,4-trimethoxybenzyl)piperazine was dissolved in 50 ml. of anhydrous diethyl ether and to the resultant solution was added 4 g. of pyridine. To the mixture was added dropwise 6 g. of ethyl chloroformate dissolved in 10 ml. of anhydrous diethyl ether over a period of about 30 minutes with ice cooling while the internal temperature was kept at 10° - 15°C. The mixture was further stirred at room temperature and filtered off to separate an insoluble matter. The filtrate was evaporated to give crude N-(α-cyano-2,3,4-trimethoxybenzyl)-N'-ethoxycarbonylpiperazine as an oily substance. This product was dissolved in toluene and the resultant solution was saturated with dry hydrochloric gas to separate crystal which was collected by filtration. Recrystallization from tetrahydrofuran-methanol afforded 14 g. of crystal having a melting point of 137.5° - 139.0°C.

Workup

  1. additionTo the mixture was added dropwise 6 g
  2. filtrationfiltered off
  3. customto separate an insoluble matter
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-1a3447566e994eccb21d02010a159c7a
Source dataset
uspto-grants-1976_06
Patent number
US03962247

Reaction notes

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