Potassium Iodide → HCID 86736638, compound

HRID 1863035Notes

Reaction equation

HRID 1863035 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:8](=[O:9])[N:7]([CH2:10][CH3:11])[N:6]=[N:5]1.Cl.[O:13]=[C:14]([N:17]([C:24]1([C:30]([O:32][CH3:33])=[O:31])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][CH3:16].[C:34](=[O:37])([O-:36])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[C:30]([OH:32])(=[O:31])[C:34]([OH:36])=[O:37].[CH2:10]([N:7]1[C:8](=[O:9])[N:4]([CH2:3][CH2:2][N:27]2[CH2:28][CH2:29][C:24]([N:17]([C:14](=[O:13])[CH2:15][CH3:16])[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)([C:30]([O:32][CH3:33])=[O:31])[CH2:25][CH2:26]2)[N:5]=[N:6]1)[CH3:11]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 30179061-(2-Chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-oneHCID 1229818061085-87-8

Product 1

HCID 86736638HCID 86736638, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.6 parts of 1-(2-chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one, 6.4 parts of methyl 4-[N-(1-oxopropyl)N-phenylamino]-4-piperidinecarboxylate hydrochloride, 4 parts of sodium carbonate, 0.1 parts of potassium iodide and 240 parts of 4-methyl-2-pentanone is stirred and refluxed overnight with water-separator. The reaction mixture is cooled and poured onto water. The organic phase is separated, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is converted into the ethanedioate salt in 2-propanone. The salt is filtered off and dried, yielding 1.5 parts (13%) of methyl 1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-4-[(1-oxopropyl)phenylamino]-4-piperidinecarboxylate ethanedioate (2:3); mp. 158.9° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. additionpoured onto water
  3. customThe organic phase is separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. filtrationThe salt is filtered off
  12. customdried

Sources & evidence

ORD record
ord-bbfd417353a14755bf12fac04c2ec573
Source dataset
uspto-grants-1979_09
Patent number
US04167574

Reaction notes

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