Pyridinium hydrochloride → HCID 69061413, compound

HRID 734857Notes

Reaction equation

HRID 734857 reaction equation
[I:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:4]([O:16]C)[CH:3]=1.Cl.[NH+]1C=CC=CC=1>C(Cl)Cl>[I:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:4]([OH:16])[CH:3]=1

Participants

4

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 69058169HCID 69058169, compound

Product 1

HCID 69061413HCID 69061413, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.10 g (8.93 mmol) of 1-[2-(4-iodo-2-methoxyphenoxy)ethyl]pyrrolidine and 4.50 g (38.94 mmol) of pyridinium hydrochloride was heated to 200° C.-250° C. for 5 minutes, cooled to RT, and combined with DCM. The organic phase was washed with water and saturated aqueous NaCl solution, dried over sodium sulfate, and evaporated down in vacuo. The residue was stirred with acetonitrile, and the precipitate was filtered off and dried in vacuo. Yield: 0.75 g (25% of theoretical); C12H16INO2 (M=333.165); calc.: molpeak (M+H)+334; found: molpeak (M+H)+: 334; HPLC-MS: 5.02 minutes (method A).

Workup

  1. temperaturewas heated to 200° C.-250° C. for 5 minutes
  2. washThe organic phase was washed with water and saturated aqueous NaCl solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated down in vacuo
  5. filtrationthe precipitate was filtered off
  6. customdried in vacuo
  7. custom5.02 minutes (method A)

Sources & evidence

ORD record
ord-166ff37f91c44b57bb54dc6d0831e4e2
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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