Potassium Iodide → HCID 13676771, compound

HRID 1863037Notes

Reaction equation

HRID 1863037 reaction equation
[CH2:1]([N:3]1[C:7](=[O:8])[NH:6][N:5]=[N:4]1)[CH3:2].Cl[CH:10]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:11][N:12]1[CH2:17][CH2:16][C:15]([N:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22](=[O:25])[CH2:23][CH3:24])([CH2:18][O:19][CH3:20])[CH2:14][CH2:13]1.[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>O.CN(C)C=O>[CH2:1]([N:3]1[C:7](=[O:8])[N:6]([CH:10]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:11][N:12]2[CH2:17][CH2:16][C:15]([N:21]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:22](=[O:25])[CH2:23][CH3:24])([CH2:18][O:19][CH3:20])[CH2:14][CH2:13]2)[N:5]=[N:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 12782361HCID 12782361, compoundHCID 1354729431-ethyl-1,2-dihydro-5H-tetrazol-5-one

Product 1

HCID 13676771HCID 13676771, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3 parts of 1-ethyl-1,4-dihydro-5H-tetrazol-5-one, 8 parts of N-[1-(2-chloro-2-phenylethyl)-4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide, 0.2 parts of potassium iodide, 5 parts of sodium carbonate and 135 parts of N,N-dimethylformamide is stirred and heated overnight at 70° C. The reaction mixture is cooled to room temperature and 150 parts of water are added. The product is extracted three times with methylbenzene. The combined extracts are dried, filtered and evaporated. The solid 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 crystallized from a mixture of petroleum-ether and 2,2'-oxybispropane. The product is filtered off and dried, yielding 5.7 parts (65%) of N-{1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)-2-phenylethyl]-4-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide; mp. 125.7° C.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionThe product is extracted three times with methylbenzene
  3. customThe combined extracts are dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe solid residue is purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe residue is crystallized from a mixture of petroleum-ether and 2,2'-oxybispropane
  11. filtrationThe product is filtered off
  12. customdried

Sources & evidence

ORD record
ord-6735b1d9eb734f2f9bd1f7259d364f82
Source dataset
uspto-grants-1979_09
Patent number
US04167574

Reaction notes

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