Water → HCID 21505565, compound

HRID 1287615Notes

Reaction equation

HRID 1287615 reaction equation
[CH3:1][S: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](Cl)(=[O:44])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].O.[OH-].[NH4+]>C(Cl)(Cl)Cl.C1C=CC=CC=1>[CH3:1][S: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:44])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:21][CH2:22]3)[C:7]=2[CH:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8206Palmitoyl chlorideHCID 14923Ammonium HydroxideHCID 1475773-{4-[8-(Methylsulfanyl)-10,11-dihydrodibenzo[b,f]thiepin-10-yl]piperazin-1-yl}propan-1-ol

Product 1

HCID 21505565HCID 21505565, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 14.0 grams of 8-methylthio-10-[4-(3-hydroxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin in a mixture of 20 milliliters of chloroform and 60 milliliters of benzene was added 19.2 grams of palmitoyl chloride (hexadecanoyl chloride) and the mixture was allowed to stand at room temperature overnight. Thereafter the mixture was heated at a temperature of 60°C for a period of 2 hours. After cooling, the mixture was added to 100 milliliters of water containing 10 milliliters of concentrated aqueous ammonium hydroxide solution, and the mixture was extracted with benzene. The extract was then washed with water, dried over anhydrous potassium carbonate, and the solvent was evaporated therefrom. The residue which included the desired ester was dissolved as completely as possible in benzene and the solution was subjected to chromatographic separation in an alumina column which was then eluted with benzene. From the benzene extract, 14.4 grams of pure 8-methylthio-10-[4-(3-hexadecanoyloxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin was recovered. The palmitic acid with which the product was contaminated was substantially completely adsorbed on the alumina column. The crude base was converted into the crystalline di(hydrogen maleate) in accordance with the general procedure described in the foregoing Examples. The yield of the salt which, after recrystallization from acetone, had a melting point of 126°-127°C, was 14.4 grams. The pure base was recovered in the form of a colorless viscous liquid by subsequent treatment of the salt with a dilute aqueous ammonium hydroxide solution and extraction with benzene.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with benzene
  3. washThe extract was then washed with water
  4. dry with materialdried over anhydrous potassium carbonate
  5. customthe solvent was evaporated
  6. dissolutionwas dissolved as completely as possible in benzene
  7. customthe solution was subjected to chromatographic separation in an alumina column which
  8. washwas then eluted with benzene
  9. extractionFrom the benzene extract
  10. custom14.4 grams of pure 8-methylthio-10-[4-(3-hexadecanoyloxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin was recovered
  11. customThe yield of the salt which, after recrystallization from acetone
  12. customThe pure base was recovered in the form of a colorless viscous liquid by subsequent treatment of the salt with a dilute aqueous ammonium hydroxide solution and extraction with benzene

Sources & evidence

ORD record
ord-f4843e2e747d4bc0a16ad45771101e68
Source dataset
uspto-grants-1976_10
Patent number
US03985750

Reaction notes

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