Potassium Carbonate → HCID 54508961, compound

HRID 635170Notes

Reaction equation

HRID 635170 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH2:17]1[CH:27]2[N:21]([C:22]3[CH:35]=[CH:34][CH:33]=[CH:32][C:23]=3[O:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=32)[CH2:20][CH2:19][NH:18]1>CC(=O)CC.C1C=CC=CC=1>[CH2:9]([O:8][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][N:18]1[CH2:19][CH2:20][N:21]2[C:22]3[CH:35]=[CH:34][CH:33]=[CH:32][C:23]=3[O:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[CH:27]2[CH2:17]1)[CH3:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 21258045HCID 21258045, compound

Product 1

HCID 54508961HCID 54508961, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Ethyl 5-bromopentanoate (1.66 g, 0.0079 mol) and potassium carbonate (1.75 g, 0.0127 mol) were added to a solution of 1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrazino[1,2-d][1,4]-oxazepine (1.6 g, 0.0063 mol prepared similarly as described in Neth. Appl. 6709520, Chem. Abs. 70, 115192 (1969)) in 2-butanone (45 ml) and the reaction mixture was heated at 70-80° C. for 17 h. The mixture was diluted with benzene (50 ml), the solid was filtered off, washed with benzene (2×10 ml) and the filtrate was evaporated in vacuo. The residue (3.2 g) was purified by column chromatography on silica gel (100 g) using benzene and a mixture of benzene and chloroform (1:1) as eluents to afford 2.35 g (97%) crude 5-(1,3,4,14b-tetrahydro-2H-dibenzo[b,f]-pyrazino[1,2-d][1,4]oxazepin -2-yl)pentanoic acid ethyl ester.

Workup

  1. customprepared similarly
  2. filtrationthe solid was filtered off
  3. washwashed with benzene (2×10 ml)
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue (3.2 g) was purified by column chromatography on silica gel (100 g)
  6. additiona mixture of benzene and chloroform (1:1) as eluents

Sources & evidence

ORD record
ord-79c588c6f4be4ec1a219cde64930b62e
Source dataset
uspto-grants-2001_02
Patent number
US06187770B1

Reaction notes

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