Potassium Iodide → HCID 67922706, compound

HRID 1110394Notes

Reaction equation

HRID 1110394 reaction equation
[NH2:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]2[O:15][CH3:16])=[O:7])=[C:4]([O:20][CH3:21])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].Cl[CH2:31][CH2:32][CH2:33][C:34]([N:36]1[CH:41]([CH3:42])[CH2:40][CH2:39][CH2:38][CH:37]1[CH3:43])=[O:35]>O.CC(C)CC(=O)C>[NH2:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:31][CH2:32][CH2:33][C:34]([N:36]3[CH:41]([CH3:42])[CH2:40][CH2:39][CH2:38][CH:37]3[CH3:43])=[O:35])[CH2:11][C@H:10]2[O:15][CH3:16])=[O:7])=[C:4]([O:20][CH3:21])[CH:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 4608817HCID 4608817, compoundHCID 98616214-Amino-5-chloro-2-methoxy-N-[(3R,4S)-3-methoxypiperidin-4-YL]benzamide

Product 1

HCID 67922706HCID 67922706, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4.5 parts of cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)benzamide, 2.12 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone was stirred and refluxed for 15 minutes using a water separator. Then there were added 3.92 parts of 1-(4-chloro-1-oxobutyl)-2,6-dimethylpiperidine and stirring was continued first for 3 hours at reflux and then overnight at room temperature. Water was added. The product was filtered off and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 5.25 parts (70.7%) of cis-4-amino-5-chloro-N-[1-[4-(2,6-dimethyl-1-piperidinyl)-4-oxobutyl]3-methoxy-4-piperidinyl]-2-methoxybenzamide; mp. 202.1° C. (compound 47).

Workup

  1. temperaturerefluxed for 15 minutes
  2. stirringstirring
  3. temperatureat reflux
  4. customovernight
  5. customat room temperature
  6. filtrationThe product was filtered off
  7. custompurified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from acetonitrile
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-9bc8c5afbeb44b1294e42d8699a52cd8
Source dataset
uspto-grants-1990_12
Patent number
US04975439

Reaction notes

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