Chloroform → HCID 3058319, compound

HRID 1758920Notes

Reaction equation

HRID 1758920 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13]Cl)[CH:10]([CH2:15]Cl)[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[CH:23]=1.C(Cl)(Cl)Cl.[O:28]1CCOCC1>[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH2:12][CH2:13][O:28][CH2:15][CH:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 312751,4-DioxaneHCID 20533044HCID 20533044, compound

Product 1

HCID 3058319HCID 3058319, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 20 g 7-chloro-1-(β-chloroethyl)2-chloromethyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine in 100 ml dioxane and 250 ml of 6% sodium hydroxide solution is heated under reflux for a period of about 5.5 hours. After heating the solution, the substance is isolated from chloroform under vacuum and subsequently purified chromatographically using aluminum oxide (activity degree II) as absorbent and methylene chloride as eluant. 12.8 g 1,2,4,4a-tetrahydro-9-chloro-7-phenyl-5H[1,4]oxazino-[4,3-a][1,4]benzodiazepine as an oil is obtained. The maleanate having a melting point of 143° to 145° C. is crystallized from isopropanol/ether. The basic compound crystallized from hexane melts at 156°-158° C.

Workup

  1. temperatureunder reflux for a period of about 5.5 hours
  2. temperatureAfter heating the solution
  3. customsubsequently purified chromatographically using aluminum oxide (activity degree II) as absorbent and methylene chloride as eluant

Sources & evidence

ORD record
ord-3f296e3ffd33485e8a9967d1d3e1fe4d
Source dataset
uspto-grants-1982_07
Patent number
US04338314

Reaction notes

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