Morpholine → 2-(2-Hydroxy-3-morpholinopropyl)-1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine

HRID 2260142Notes

Reaction equation

HRID 2260142 reaction equation
Cl[CH2:2][CH:3]([OH:24])[CH2:4][N:5]1[CH2:23][CH2:22][N:8]2[C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=3[CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH:7]2[CH2:6]1.C(=O)([O-])[O-].[Na+].[Na+].[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>[I-].[Na+].CC(C)CC(=O)C>[OH:24][CH:3]([CH2:2][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)[CH2:4][N:5]1[CH2:23][CH2:22][N:8]2[C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=3[CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH:7]2[CH2:6]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 10340Sodium CarbonateHCID 18999768HCID 18999768, compound

Product 1

HCID 189997572-(2-Hydroxy-3-morpholinopropyl)-1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepineYield 87.1%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

0.5 g of 2-(3-chloro-2-hydroxypropyl)-1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine (prepared as described in Example 41), 2.7 g of sodium carbonate, 0.014 g of sodium iodide and 0.254 g of morpholine were added to 10 ml of 4-methyl-2-pentanone, and the mixture was heated under reflux for 2 hours. At the end of this time, the reaction mixture was filtered, and then the filtrate was concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel, using ethyl acetate as the eluent, to afford 0.50 g (yield 87%) of the title compound as a colorless foam.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. filtrationAt the end of this time, the reaction mixture was filtered
  4. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-e9bfac6a13c44cfabbd49ba73bed209e
Source dataset
uspto-grants-1995_12
Patent number
US05476848

Reaction notes

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