Water → HCID 67045723, compound

HRID 1810606Notes

Reaction equation

HRID 1810606 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:19]=[CH:18][C:9]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1.[CH2:20]([NH2:24])[CH2:21][CH2:22]C.O.[OH-].[Na+].[C:28](#N)C>>[CH3:22][CH2:21][CH:20]([NH:24][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:19]=[CH:18][C:9]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1)[CH3:28]

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 8007ButylamineHCID 14798Sodium HydroxideHCID 10934655HCID 10934655, compound

Product 1

HCID 67045723HCID 67045723, compound

Conditions

Temperature
70 °C

Procedure

10 g (36 mmol) 4-(3-chloropropoxy)benzophenone was dissolved in 100 mL acetonitrile. 26.3 g (0.36 mol) n.-butyl amine was added and the mixture was heated to 70° C. for 30 hours. The solvent was evaporated under reduced pressure and the residue was treated with 500 mL water. The pH was adjusted to pH=1. The mixture was stirred for one hour at 40° C. The mixture was cooled to 10° C. and the precipitated compounds were isolated by filtration. The precipitate was treated with 200 mL water and the pH was adjusted to 12, using a 1 N NaOH-solution. The mixture was extracted with 200 mL methylene chloride. The organic fraction was dried over MgSO4 and evaporated under reduced pressure. The crude 4-[(3-butylamino)propoxy]benzophenone was purified by preparative column chromatography on a SVP D40 Merck-Np column, using a gradient elution from methylene chloride to methanol at a flow rate of 40 mL per minute. 4.4 g of 4-[(3-butylamino)propoxy]benzophenone was isolated.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was treated with 500 mL water
  3. temperatureThe mixture was cooled to 10° C.
  4. customthe precipitated compounds were isolated by filtration
  5. extractionThe mixture was extracted with 200 mL methylene chloride
  6. dry with materialThe organic fraction was dried over MgSO4
  7. customevaporated under reduced pressure
  8. customThe crude 4-[(3-butylamino)propoxy]benzophenone was purified by preparative column chromatography on a SVP D40 Merck-Np column
  9. washa gradient elution from methylene chloride to methanol at a flow rate of 40 mL per minute

Sources & evidence

ORD record
ord-0c833bb58ee6403bac36c898b0a50c8d
Source dataset
uspto-grants-2013_01
Patent number
US08362101B2

Reaction notes

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