Ammonia → HCID 18349551, compound

HRID 2268258Notes

Reaction equation

HRID 2268258 reaction equation
C([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][CH2:14][CH2:15][NH:16][C:17]([C:20]1[CH:25]=[CH:24][C:23](Cl)=[CH:22][CH:21]=1)([CH3:19])[CH3:18])C1C=CC=CC=1.N>C1COCC1>[NH:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][CH2:14][CH2:15][NH:16][C:17]([CH3:19])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:18]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 18349547HCID 18349547, compound

Product 1

HCID 18349551HCID 18349551, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-35 °C

Procedure

A solution of the final product from Example 86 (200 mg) in dry THF (5 ml) was added to liquid ammonia (15 ml) (purified by treating the liquid ammonia with sodium and distilling the ammonia into another flask). The mixture was cooled in a dry ice acetone bath at −35° C., in a flask fitted with an acetone dry ice condenser, and small pieces of sodium were added until the blue colour persisted. After 15 minutes ammonium chloride (0.1 g) was added and the ammonia allowed to evaporate. Ethanol (10 ml) was added to the mixture followed by water (10 ml) and the solvent largely removed under reduced pressure. The residue was diluted with water and extracted with dichloromethane to give a residue which was purified by flash column chromatography on silica using methanol/ethyl acetate (1:1) as the mobile phase to give 3-(imidazol-2-yl)-N-(1-methyl-1-phenylethyl)propylamine as an oil.

Workup

  1. custompurified
  2. additionby treating the liquid ammonia with sodium
  3. distillationdistilling the ammonia into another flask)
  4. customfitted with an acetone dry ice condenser
  5. additionsmall pieces of sodium were added until the blue colour
  6. additionAfter 15 minutes ammonium chloride (0.1 g) was added
  7. customto evaporate
  8. additionEthanol (10 ml) was added to the mixture
  9. customthe solvent largely removed under reduced pressure
  10. additionThe residue was diluted with water
  11. extractionextracted with dichloromethane
  12. customto give a residue which
  13. customwas purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-c91bb43fdf094db1bac944519ae346f3
Source dataset
uspto-grants-2001_12
Patent number
US06326500B1

Reaction notes

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