Potassium Iodide → HCID 19883499, compound

HRID 1088388Notes

Reaction equation

HRID 1088388 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[CH2:13]([N:15]([CH2:29][CH3:30])[CH2:16][CH2:17][O:18][CH:19]1[C:24]([O:27][CH3:28])([O:25][CH3:26])[CH2:23][CH2:22][NH:21][CH2:20]1)[CH3:14].C(N(CC)CC)C.[I-].[K+]>CN(C)C=O>[CH2:29]([N:15]([CH2:13][CH3:14])[CH2:16][CH2:17][O:18][CH:19]1[C:24]([O:27][CH3:28])([O:25][CH3:26])[CH2:23][CH2:22][N:21]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=2)[CH2:20]1)[CH3:30]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 743911-(3-Chloropropoxy)-4-fluorobenzeneHCID 19883537HCID 19883537, compound

Product 1

HCID 19883499HCID 19883499, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7.5 parts of 1-(3-chloropropoxy)-4-fluorobenzene, 10.5 parts of N,N-diethyl-2-[(4,4-dimethoxy-3-piperidinyl)oxy]ethanamine, 7 parts of N,N-diethylethanamine, 1 part of potassium iodide and 90 parts of N,N-dimethylformamide was stirred for 17 hours at 60° C. The reaction mixture was poured onto water and the product was extracted with trichloromethane. The extract was washed with water, 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) saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in acetonitrile and 2-propanol. The whole was evaporated and the residue was taken up in acetonitrile. The solution was evaporated, yielding 14 parts (75%) of N,N-diethyl-2-[[1-[3-(4-fluorophenoxy)propyl-]-4,4-dimethoxy-3-piperidinyl]oxy]ethanamine as a residue (intermediate 115).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionthe product was extracted with trichloromethane
  3. washThe extract was washed with water
  4. customdried
  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) saturated with ammonia
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe whole was evaporated
  12. customThe solution was evaporated

Sources & evidence

ORD record
ord-61f5287fbb174b4f999f9991bde9f761
Source dataset
uspto-grants-1990_10
Patent number
US04962115

Reaction notes

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