Toluene → HCID 18999753, compound

HRID 2210814Notes

Reaction equation

HRID 2210814 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][CH2:24][CH2:25][CH2:26][CH2:27][OH:28].Br[CH2:30][C:31]([O:33][CH3:34])=[O:32].[C:35]1(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][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

5

Reactant 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 18999739HCID 18999739, compound

Product 1

HCID 18999753HCID 18999753, compoundYield 18%

Conditions

Temperature
40 °C

Procedure

060 g of a 55% w/w dispersion of sodium hydride in mineral oil was added to a solution of 0.40 g of 6-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2 -a]azepin-2-yl)hexanol (prepared as described in Example 18) dissolved in 10 m of toluene, under an atmosphere of nitrogen. The mixture was stirred at 40° C. for 2 hours and then cooled with ice, after which 0.229 g of methyl bromoacetate were added, and the mixture was stirred at 40° C. for a further 4 hours. At the end of this time, the reaction mixture was filtered, and the solvent was removed from the filtrate by evaporation under reduced pressure. The residue was subjected column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to afford 90 mg (yield 18%) of the title compound as an oil.

Workup

  1. temperaturecooled with ice
  2. stirringthe mixture was stirred at 40° C. for a further 4 hours
  3. filtrationAt the end of this time, the reaction mixture was filtered
  4. customthe solvent was removed from the filtrate by evaporation under reduced pressure
  5. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-0c5a68e3ab1042c1a5b0fd9a8e7578a9
Source dataset
uspto-grants-1995_10
Patent number
US05461051

Reaction notes

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