Acetonitrile → HCID 67045661, compound

HRID 1810607Notes

Reaction equation

HRID 1810607 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](N)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(#[N:29])C>>[CH3:20][CH2:21][CH:22]([NH:29][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)[CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 8102HexylamineHCID 10934655HCID 10934655, compound

Product 1

HCID 67045661HCID 67045661, compound

Conditions

Temperature
70 °C

Procedure

10 g (36 mmol) 4-(3-chloropropoxy)benzophenone was dissolved in 100 mL acetonitrile. 36.4 g (0.36 mol) n.-hexyl amine was added and the mixture was heated to 70° C. for 20 hours. The solvent was evaporated under reduced pressure. The oily residue was treated with 500 mL water. The mixture was acidified to pH=1 and stirred for 16 hours at room temperature. The precipitated compounds were isolated by filtration and washed with 200 mL 1 N HCl. The precipitate was treated with 200 mL 1 N NaOH. The mixture was extracted with 200 mL methylene chloride. The organic fraction was dried over MgSO4 and the solvent was evaporated under reduced pressure. The crude 4-[(3-hexylamino)propoxy]benzophenone was purified by preparative column chromatography on a Prochrom LC80 column, using Kromasil Si 60A 10 mm as silica and a gradient elution from methylene chloride to methylene chloride/methanol 68/32 at a flow rate of 150 mL per minute. 3.9 g of 4-[(3-hexylamino)propoxy]benzophenone was isolated.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionThe oily residue was treated with 500 mL water
  3. customThe precipitated compounds were isolated by filtration
  4. washwashed with 200 mL 1 N HCl
  5. additionThe precipitate was treated with 200 mL 1 N NaOH
  6. extractionThe mixture was extracted with 200 mL methylene chloride
  7. dry with materialThe organic fraction was dried over MgSO4
  8. customthe solvent was evaporated under reduced pressure
  9. customThe crude 4-[(3-hexylamino)propoxy]benzophenone was purified by preparative column chromatography on a Prochrom LC80 column
  10. washa gradient elution from methylene chloride to methylene chloride/methanol 68/32 at a flow rate of 150 mL per minute

Sources & evidence

ORD record
ord-d98c0524b20543d098969eb30d674c99
Source dataset
uspto-grants-2013_01
Patent number
US08362101B2

Reaction notes

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