Hydrochloric Acid → HCID 13065369, compound

HRID 358254Notes

Reaction equation

[CH3:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10](Cl)[C:4]=2[CH:3]=1.[OH:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)C.O>[CH3:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]([N:24]3[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][OH:18])[CH2:22][CH2:23]3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In this example, 3.7 g of crude crystals of 2-methyl-11-chloro-6,11-dihydrodibenz [b,e] oxepin obtained from 3.6 g of 2-methyl-6,11-dihydrodibenz [b,e] oxepinone-11 in the same manner as in Example 1 are dissolved in 60 ml of toluene and the solution is dropwise added to a solution of 9.8 g of 1-(2-hydroxyethyl) piperazine in 20 ml of toluene, followed by heating for 2 hours at 80° C. After completion of the reaction, 30 ml of water is added thereto, and the pH of the solution is adjusted to 2.0 with concentrated hydrochloric acid. Then, a toluene layer is discarded, and 20 ml of ethyl ether is added to an aqueous layer, followed by readjusting the pH of the solution to 10.5 with a 10 N sodium hydroxide aqueous solution. The aqueous layer is discarded, and the ethyl ether layer is dehydrated and concentrated under reduced pressure. The residue is purified through silica gel chromatography. Concentration of the main fractions gives 4.0 g of 2-methyl-11-[4-(2-hydroxyethyl)-1-piperazinyl]-6,11-dihydrodibenz [b,e] oxepin [compound 37] in an oily free base in a yield of 79%.

Workup

additionis added
concentrationconcentrated under reduced pressure
customThe residue is purified through silica gel chromatography

Sources & evidence

ORD record: ord-f6241588fd44492faba72ba7b35a2b5c
Source dataset: uspto-grants-1984_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04465835

Reaction notes

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