Methane → Oxatomide monohydrate

HRID 355003

Reaction equation

HRID 355003 reaction equation
[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C>CC(O)C>[OH2:26].[C:27]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:10][CH2:9]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 297MethaneHCID 4615Oxatomide

Product 1

HCID 20506331Oxatomide monohydrate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

50 Parts of 1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one are dissolved in 200 of 2-propanol while stirring and heating. The solution is stirred with 2.5 parts of activated charcoal. The latter is filtered off and upon cooling to room temperature, the product is crystallized. It is filtered off and converted into the hydrochloride salt in 2-propanol. The salt is filtered off, washed twice with 2-propanol and dried overnight in vacuo at 60° C. It is dissolved in 320 parts of methanol and the free base is liberated in the conventional manner with a sodium hydroxide solution 5 N. The whole is concentrated to a volume of about 150 parts. The precipitated product is filtered off, washed with 500 parts of water and dissolved in 120 parts of 2-propanol. The solution is stirred and heated with 1 part of activated charcoal. The latter is filtered off over hyflo while hot. The filtrate is cooled to room temperature while stirring. The precipitated product is filtered off and dried over week-end in vacuo at 60° C., yielding 21.49 parts of 1{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one hydrate; mp. 156.6° C.

Workup

  1. temperatureheating
  2. filtrationThe latter is filtered off
  3. customthe product is crystallized
  4. filtrationIt is filtered off
  5. filtrationThe salt is filtered off
  6. washwashed twice with 2-propanol
  7. customdried overnight in vacuo at 60° C
  8. dissolutionIt is dissolved in 320 parts of methanol
  9. concentrationThe whole is concentrated to a volume of about 150 parts
  10. filtrationThe precipitated product is filtered off
  11. washwashed with 500 parts of water
  12. dissolutiondissolved in 120 parts of 2-propanol
  13. stirringThe solution is stirred
  14. temperatureheated with 1 part of activated charcoal
  15. filtrationThe latter is filtered off over hyflo while hot
  16. temperatureThe filtrate is cooled to room temperature
  17. stirringwhile stirring
  18. filtrationThe precipitated product is filtered off
  19. customdried over week-end in vacuo at 60° C.

Sources & evidence

ORD record
ord-e08e10ff87b9413d85ab3000de2a2a9f
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Linked notes

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