Hydrochloric Acid → HCID 62291536, compound

HRID 1677558Notes

Reaction equation

HRID 1677558 reaction equation
C1N2CN3CN(C2)C[N:2]1C3.[I-].[Na+].[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH2:27]Cl)[CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>ClCCl.CO.C(OCC)C>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH2:27][NH2:2])[CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 5238Sodium IodideHCID 129385594-(Benzyloxy)-2-(chloromethyl)pyridine

Product 1

HCID 62291536HCID 62291536, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1.5 g (10.78 mmol) of hexamethylenetetramine and then 1.3 g of sodium iodide are added to 2.1 g (8.99 mmol) of 4-(benzyloxy)-2-(chloromethyl)pyridine (described in stage A) in 60 ml of dichloromethane. The reaction medium is heated at reflux for 12 hours and then concentrated under reduced pressure. The residue obtained is taken up in 45 ml of methanol. 7.5 ml (89.90 mmol) of a 12N hydrochloric acid solution are added. The reaction medium is heated at reflux for 16 hours. After addition of ethyl ether, the precipitate obtained is filtered off and then taken up in a saturated aqueous sodium carbonate solution. The aqueous phase is extracted with ethyl acetate, dried over sodium sulfate and then concentrated under reduced pressure. 1.1 g of a beige oil are collected. Mass spectrometry (ES+Mode): MH+=215

Workup

  1. temperatureThe reaction medium is heated
  2. temperatureat reflux for 12 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue obtained
  5. temperatureThe reaction medium is heated
  6. temperatureat reflux for 16 hours
  7. customthe precipitate obtained
  8. filtrationis filtered off
  9. extractionThe aqueous phase is extracted with ethyl acetate
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. custom1.1 g of a beige oil are collected

Sources & evidence

ORD record
ord-f46618eedc9540c388fbb79c6f22fb88
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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