Sodium Hydroxide → HCID 23318332, compound

HRID 1981974Notes

Reaction equation

HRID 1981974 reaction equation
[CH3:1][N:2]1[CH2:23][CH2:22][N:5]2[C:6]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:7]=3[C:8]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)=[N+:9]([O-])[CH2:10][CH:4]2[CH2:3]1.P(Cl)(Cl)[Cl:25].[OH-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][N:2]1[CH2:23][CH2:22][N:5]2[C:6]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:7]=3[C:8]([C:12]3[O:13][C:14]([Cl:25])=[CH:15][CH:16]=3)=[N:9][CH2:10][CH:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24387Phosphorus trichlorideHCID 30712577-(Furan-2-yl)-3,9-dimethyl-6-oxo-1,2,3,4,4a,5-hexahydro-6lambda~5~-pyrazino[1,2-a][1,4]benzodiazepine

Product 1

HCID 23318332HCID 23318332, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

9.3 g of 1,2,3,4,4a,5-hexahydro-3,9-dimethyl-7-(2-furyl)-pyrazino[1,2-a][1,4]benzodiazepine 6-oxide (prepared analogously to Example 5) are heated under reflux in 150 ml of chloroform with 17 ml of phosphorus trichloride for 1 hour. The reaction mixture is then treated with aqueous sodium hydroxide solution and worked up. The resulting crude product is separated into its components by chromatography on aluminium oxide of activity level II, using methylene chloride/chloroform. 1.7 g of the less polar 1,2,3,4,4a,5-hexahydro-3,9-dimethyl-7-(5-chloro-2-furyl)-pyrazino[1,2-a][1,4]benzodiazepine are thereby initially obtained in the first fraction, and the product is isolated as an oil (IR: 1,615 cm-1C=N) (b). 5 g of the more highly polar 1,2,3,4,4a,5-hexahydro-3,9-dimethyl-7-(2-furyl)-pyrazino[1,2-a][1,4]benzodiazepine (a) are then obtained.

Workup

  1. temperatureare heated
  2. customThe resulting crude product is separated into its components by chromatography on aluminium oxide of activity level II

Sources & evidence

ORD record
ord-847b2a73de7243b3981f322096bdc0be
Source dataset
uspto-grants-1986_06
Patent number
US04594436

Reaction notes

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