Octanoyl chloride → HCID 21505558, compound

HRID 1287613Notes

Reaction equation

HRID 1287613 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:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>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: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

5

Reactant 2

HCID 8124Octanoyl chlorideHCID 1475773-{4-[8-(Methylsulfanyl)-10,11-dihydrodibenzo[b,f]thiepin-10-yl]piperazin-1-yl}propan-1-ol

Product 1

HCID 21505558HCID 21505558, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

In accordance with the general procedure described in the foregoing Examples, 14.0 grams of 8-methylthio-10-[4-(3-hydroxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin was reacted with 12.2 grams of caprylyl chloride (octanoyl chloride) in a mixture of 20 milliliters of chloroform and 60 milliliters of benzene. After the reaction mixture had been allowed to stand for 4 days at room temperature, the reaction mixture was heated to a temperature of 60°C and further treated as described in the preceding Example. The recovered crude 8-methylthio-10-[4-(3-octanoyloxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin was thereafter converted into the crystalline di(hydrogen maleate) as described in the foregoing Example. The salt was recovered in a yield of 13.7 grams and, after recrystallization from acetone, had a melting point of 122°-123°C. The pure base was recovered in the form of a viscous oil by treatment of the pure salt with a dilute aqueous solution of ammonium hydroxide as described in the foregoing Example.

Workup

  1. additionfurther treated
  2. customThe recovered crude 8-methylthio-10-[4-(3-octanoyloxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin
  3. customThe salt was recovered in a yield of 13.7 grams
  4. customafter recrystallization from acetone
  5. customThe pure base was recovered in the form of a viscous oil by treatment of the pure salt with a dilute aqueous solution of ammonium hydroxide

Sources & evidence

ORD record
ord-522442931e4a4ce393a570d552b1071a
Source dataset
uspto-grants-1976_10
Patent number
US03985750

Reaction notes

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