Octanoyl chloride → HCID 21505572, compound

HRID 1287617Notes

Reaction equation

HRID 1287617 reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]2[S:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH2:11][CH:10]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][OH:28])[CH2:21][CH2:20]3)[C:9]=2[CH:29]=1)[CH2:2][CH2:3][CH3:4].[C:30](Cl)(=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C(O)(=O)/C=C\C(O)=O>C1C=CC=CC=1.C(Cl)(Cl)Cl.CC(C)=O.[OH-].[NH4+]>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]2[S:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH2:11][CH:10]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][O:28][C:30](=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:21][CH2:20]3)[C:9]=2[CH:29]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 3

HCID 8124Octanoyl chlorideHCID 444266Maleic AcidHCID 21505566HCID 21505566, compound

Product 1

HCID 21505572HCID 21505572, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 241BenzeneSolventHCID 6212ChloroformSolventHCID 14923Ammonium HydroxideSolvent

Procedure

In accordance with the general procedure described in the foregoing Examples, 4.1 grams of 8-(n-butyl)-10-[4-(3-hydroxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin was reacted with 3.2 grams of caprylyl chloride (octanoyl chloride) in a mixture of 18 milliliters of benzene and 7 milliliters of chloroform. A solution of 2.3 grams of maleic acid in 25 milliliters of acetone was then added to the mixture and the resulting 8-(n-butyl)-10-[4-(3-oxtanoyloxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin di(hydrogen maleate) which had a melting point of 113°-115°C, after recrystallization from acetone, was recovered. Its elemental analysis corresponded to the empirical formula C41H56N2O10S. The free base was obtained in the form of a colorless very viscous oil which was very soluble in vegetable oils by dissolving the salt in a dilute aqueous ammonium hydroxide solution and extracting the solution with benzene.

Workup

  1. customafter recrystallization from acetone
  2. customwas recovered
  3. customThe free base was obtained in the form of a colorless very viscous oil which
  4. extractionextracting the solution with benzene

Sources & evidence

ORD record
ord-6fa7f285c03c49d980b55938a59e805c
Source dataset
uspto-grants-1976_10
Patent number
US03985750

Reaction notes

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