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Potassium Iodide → 5-Chloro-2,3-dihydro-7-[3-[1-(3-methoxypropyl)-4-piperidinyl]-1,2,4-oxadiazol-5-yl]-4-benzofuranamine monohydrochloride

HRID 1459464
Notes
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Reaction equation

HRID 1459464 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][CH3:6].[Cl:7][C:8]1[C:16]([NH2:17])=[C:12]2[CH2:13][CH2:14][O:15][C:11]2=[C:10]([C:18]2[O:22][N:21]=[C:20]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[N:19]=2)[CH:9]=1.C(N(CC)CC)C.[I-].[K+]>CN(C)C=O>[ClH:1].[Cl:7][C:8]1[C:16]([NH2:17])=[C:12]2[CH2:13][CH2:14][O:15][C:11]2=[C:10]([C:18]2[O:22][N:21]=[C:20]([CH:23]3[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][O:5][CH3:6])[CH2:25][CH2:24]3)[N:19]=2)[CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 1189271-Chloro-3-methoxypropaneHCID 538340175-Chloro-2,3-dihydro-7-[3-(4-piperidinyl)-1,2,4-oxadiazol-5-yl]-4-benzofuranamine

Product 1

HCID 867534815-Chloro-2,3-dihydro-7-[3-[1-(3-methoxypropyl)-4-piperidinyl]-1,2,4-oxadiazol-5-yl]-4-benzofuranamine monohydrochlorideYield 22.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl (3-chloropropyl) ether (1.6 g), intermediate 4 (3.9 g), triethylamine (5 ml) and potassium iodide (a catalytic amount) in dimethylformamide (60 ml) was stirred for 48 hours at 60° C. The reaction mixture was cooled and the solvent evaporated. The residue was partitioned between CH2Cl2 and a saturated aqueous NaCl solution. The organic layer was separated, dried over MgSO4, filtered and the solvent evaporated. The residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 90/10). The desired fractions were collected and the solvent was evaporated. The residue was solidified in DIPE, filtered off, dissolved in 2-propanol and converted into the hydrochloric acid salt (1:1) with HCl/2-propanol. The precipitate was filtered off and dried, yielding 1.14 g (22.1%) of 5-chloro-2,3-dihydro-7-[3-[1-(3-methoxypropyl)-4-piperidinyl]-1,2,4-oxadiazol-5-yl]-4-benzofuranamine monohydrochloride.hemihydrate (compound 1; mp. 244.3° C.).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent evaporated
  3. customThe residue was partitioned between CH2Cl2
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 90/10)
  9. customThe desired fractions were collected
  10. customthe solvent was evaporated
  11. filtrationfiltered off
  12. dissolutiondissolved in 2-propanol
  13. filtrationThe precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-21b18d801ac145e1bc699ac175459281
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05854261

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes