Sodium Hydroxide → HCID 19095303, compound

HRID 486546Notes

Reaction equation

[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[CH2:6][CH2:7][C:8]3[CH:9]=[CH:10][N:11]([CH2:13][CH2:14][NH:15][C:16](=O)[CH3:17])[C:12]=3[C:4]=2[CH:3]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>C(O)C>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[CH2:6][CH2:7][C:8]3[CH:9]=[C:10]4[C:16]([CH3:17])=[N:15][CH2:14][CH2:13][N:11]4[C:12]=3[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N-[2-(8-Chloro-4,5-dihydro-1H-benzo[g]indol-1-yl)-ethyl]acetamide (2.9 g) was treated with 20 ml of phosphorus oxychloride under argon and the mixture was stirred at 100° C. for 30 minutes. The cooled mixture was poured on to 1500 g of ice-water and treated with 100 ml of 2N sodium hydroxide solution and 150 ml of 28% sodium hydroxide solution. The mixture was extracted once with 250 ml of methylene chloride and twice with 150 ml of methylene chloride each time, the organic phases were combined, dried with MgSO4 and freed from solvent. The residue (2.7 g) was dissolved in a 20-fold amount of ethanol and treated while hot with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There were obtained 3.2 g (83%) of 2-chloro-5,6,10,11-tetrahydro-8-methylbenzo[g]pyrazino[1,2-a]indole fumarate (1:1); m.pt.: 172°-174° C. (dec.).

Workup

extractionThe mixture was extracted once with 250 ml of methylene chloride and twice with 150 ml of methylene chloride each time
dry with materialdried with MgSO4
dissolutionThe residue (2.7 g) was dissolved in a 20-fold amount of ethanol

Sources & evidence

ORD record: ord-2f711bbe2ac347fcb5b22020182d8dfb
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292732

Reaction notes

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