Methyl Isobutyl Ketone → HCID 20506363, compound

HRID 354980Notes

Reaction equation

HRID 354980 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]1=[O:14].[C:15]1([CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[ClH:1].[ClH:1].[C:28]1([CH:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:22]2[CH2:23][CH2:24][N:25]([CH2:2][CH2:3][CH2:4][N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[O:7][C:6]3=[O:14])[CH2:26][CH2:27]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 70048BenzhydrylpiperazineHCID 100360722(3H)-Benzoxazolone, 3-(3-chloropropyl)-

Product 1

HCID 20506363HCID 20506363, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 4.9 parts of 3-(3-chloropropyl)-2(3H)-benzoxazolone, 5 parts of 1-(diphenylmethyl)piperazine, 6.4 parts of sodium carbonate and 200 parts of 4-methyl-2-pentanone is stirred and refluxed overnight with water-separator. The reaction mixture is cooled, water is added and the layers are separated. The 4-methyl-2-pentanone phase is dried, filtered and evaporated. The oily residue is dissolved in 2,2'-oxybispropane and the solution is stirred with activated charcoal. The latter is filtered off over hyflo and the clear filtrate is acidified with 2-propanol, previously saturated with gaseous hydrogen chloride. The formed hydrochloride salt is filtered off and triturated in 2-propanol. It is filtered off again and dried, yielding 3-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-2(3H)benzoxazolone dihydrochloride; mp. 212.4° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe layers are separated
  3. dry with materialThe 4-methyl-2-pentanone phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe oily residue is dissolved in 2,2'-oxybispropane
  7. stirringthe solution is stirred with activated charcoal
  8. filtrationThe latter is filtered off over hyflo
  9. filtrationThe formed hydrochloride salt is filtered off
  10. customtriturated in 2-propanol
  11. filtrationIt is filtered off again
  12. customdried

Sources & evidence

ORD record
ord-92d01644b8094384a0a9de44adf05f9b
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

Loading…