Octanoic Acid → HCID 21505582, compound

HRID 1287611Notes

Reaction equation

HRID 1287611 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH2:9][CH:8]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:19][CH2:18]3)[C:7]=2[CH:27]=1.[C:28](O)(=[O:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].O.[OH-].[NH4+]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH2:9][CH:8]([N:17]3[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][CH2:25][O:26][C:28](=[O:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:21][CH2:22]3)[C:7]=2[CH:27]=1

Participants

6

Reactant 4

HCID 379Octanoic AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 2072963-[4-(8-Methoxy-10,11-dihydrodibenzo[b,f]thiepin-10-yl)piperazin-1-yl]propan-1-ol

Product 1

HCID 21505582HCID 21505582, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 14.82 grams of 8-methoxy-10-[4-(3-hydroxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin in 50 milliliters of benzene was added 12.55 grams of caprylic acid (octanoic acid). The resulting reaction mixture was allowed to stand overnight and was then heated for 3 hours at a temperature of 60°C. After cooling, the mixture was shaken with 100 milliliters of water, 20 milliliters of concentrated aqueous ammonium hydroxide solution was then added thereto, and the mixture was extracted with a mixture of benzene and ethyl ether. The resulting extract was washed with water, dried over anhydrous potassium carbonate, and the solvent was evaporated therefrom. The residue was dissolved in 40 milliliters of acetone and added to a solution of 9.5 grams of maleic acid in 30 milliliters of acetone. On standing, 15.5 grams of crude 8-methoxy-10-]4-(3-octanoyloxypropyl)piperazino]-10,11-dihydrobenzo[b,f]thiepin di(hydrogen maleate) crystals separated therefrom. On purification by recrystallization from acetone, the di(hydrogen maleate) salt had a melting point of 130°C. The free base was recovered in the form of a viscous oil by adding the di(hydrogen maleate) to a dilute aqueous ammonium hydroxide solution and extracting the solution with benzene as described in Example 1 hereinbefore.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling
  3. additionwas then added
  4. extractionthe mixture was extracted with a mixture of benzene and ethyl ether
  5. extractionThe resulting extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous potassium carbonate
  8. customthe solvent was evaporated
  9. dissolutionThe residue was dissolved in 40 milliliters of acetone
  10. additionadded to a solution of 9.5 grams of maleic acid in 30 milliliters of acetone
  11. custom15.5 grams of crude 8-methoxy-10-]4-(3-octanoyloxypropyl)piperazino]-10,11-dihydrobenzo[b,f]thiepin di(hydrogen maleate) crystals separated
  12. customOn purification
  13. customby recrystallization from acetone
  14. customThe free base was recovered in the form of a viscous oil
  15. additionby adding the di(hydrogen maleate) to a dilute aqueous ammonium hydroxide solution
  16. extractionextracting the solution with benzene

Sources & evidence

ORD record
ord-5788ce3238cd48e09ba86ac249da8940
Source dataset
uspto-grants-1976_10
Patent number
US03985750

Reaction notes

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