Potassium Iodide → HCID 67922735, compound

HRID 2248629Notes

Reaction equation

HRID 2248629 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([N:7]([CH3:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].[NH2:15][C:16]1[C:32]([Cl:33])=[CH:31][C:19]([C:20]([NH:22][C@H:23]2[CH2:28][CH2:27][NH:26][CH2:25][C@H:24]2[O:29][CH3:30])=[O:21])=[C:18]([O:34][CH3:35])[CH:17]=1.C(N(CC)CC)C.[I-].[K+]>CN(C)C=O>[OH2:6].[NH2:15][C:16]1[C:32]([Cl:33])=[CH:31][C:19]([C:20]([NH:22][C@H:23]2[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][C:5]([N:7]([CH3:14])[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:6])[CH2:25][C@H:24]2[O:29][CH3:30])=[O:21])=[C:18]([O:34][CH3:35])[CH:17]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 98616214-Amino-5-chloro-2-methoxy-N-[(3R,4S)-3-methoxypiperidin-4-YL]benzamideHCID 16780864HCID 16780864, compound

Product 1

HCID 67922735HCID 67922735, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.54. parts of 4-chloro-N-methyl-N-phenylbutanamide, 3.14 parts of cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)benzamide, 2.45 parts of N,N-diethylethanamine, 0.1 parts of potassium iodide and 90 parts of N,N-dimethylformamide was stirred for 20 hours at 80° C. The reaction mixture was evaporated. The residue was taken up in water and sodium carbonate. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile and a small amount of water. The product was filtered off and dried, yielding 2.05 parts (40.4%) of cis-4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-3-methoxy-N-methyl-N-phenyl-1-piperidinebutanamide monohydrate; mp. 97.4° C. (compound 23).

Workup

  1. additionA mixture of 2.54
  2. customThe reaction mixture was evaporated
  3. extractionThe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (95:5 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-e735966cfde24b818e6a1b093f9af18c
Source dataset
uspto-grants-1991_08
Patent number
US05041454

Reaction notes

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