Sodium hydride → Methyl 2-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxyacetate

HRID 2260134Notes

Reaction equation

[H-].[Na+].[CH2:3]1[CH: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[N:7]2[CH2:6][CH2:5][N:4]1[CH2:22][CH2:23][OH:24].Br[CH2:26][C:27]([O:29][CH3:30])=[O:28]>C1(C)C=CC=CC=1>[CH2:3]1[CH: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[N:7]2[CH2:6][CH2:5][N:4]1[CH2:22][CH2:23][O:24][CH2:26][C:27]([O:29][CH3:30])=[O:28]

Participants

Conditions

Temperature: 40 °C

Procedure

0.478 g of a 55% w/w dispersion of sodium hydride in mineral oil was added to a solution of 1.5 g of 2-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethanol [prepared as described in step (a) or (c) above] dissolved in 20 ml of toluene, under an atmosphere of nitrogen. The mixture was then stirred at 40° C. for 2 hours, after which 0.924 g of methyl bromoacetate was added, whilst ice-cooling; the mixture was then stirred at 40° C. for a further 4 hours. At the end of this time, the reaction mixture was filtered and the filtrate was concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to afford 0.58 g (31% yield) of the title compound as an oil.

Workup

temperaturecooling
stirringthe mixture was then stirred at 40° C. for a further 4 hours
filtrationAt the end of this time, the reaction mixture was filtered
concentrationthe filtrate was concentrated by evaporation under reduced pressure
additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record: ord-0ee4c3e5e7164163ad024d7513636926
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05476848

Reaction notes

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