Potassium Iodide → HCID 86744369, compound

HRID 1110393Notes

Reaction equation

HRID 1110393 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].NC1C(Cl)=CC(C(N[C@H:23]2[CH2:28][CH2:27][NH:26][CH2:25][C@H:24]2[O:29][CH3:30])=O)=C(OC)C=1.C(N(CC)CC)C.[I-].[K+]>CN(C)C=O>[OH2:6].[CH3:30][O:29][CH:24]1[CH2:23][CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][C:5]([N:7]([CH3:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:6])[CH2:25]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 86744369HCID 86744369, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

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. customThe reaction mixture was evaporated
  2. extractionThe product was extracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from acetonitrile
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-eec52c55a0a74e8e8a3083c6f8eea4ff
Source dataset
uspto-grants-1990_12
Patent number
US04975439

Reaction notes

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