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N,N'-Dimethylethylenediamine → 2-(4-Chloro-3-(3-hydroxyoxetan-3-yl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

HRID 592678
Notes
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Reaction equation

HRID 592678 reaction equation
[C:1]1(=[O:14])[C:6]2=[CH:7][C:8]3[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=3[N:5]2[CH2:4][CH2:3][NH:2]1.Br[C:16]1[C:21]([C:22]2([OH:26])[CH2:25][O:24][CH2:23]2)=[C:20]([Cl:27])[CH:19]=[CH:18][N:17]=1.CNCCNC.CC([O-])=O.[K+]>[Cu]I.O1CCOCC1>[Cl:27][C:20]1[CH:19]=[CH:18][N:17]=[C:16]([N:2]2[CH2:3][CH2:4][N:5]3[C:13]4[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=4[CH:7]=[C:6]3[C:1]2=[O:14])[C:21]=1[C:22]1([OH:26])[CH2:25][O:24][CH2:23]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 517044Potassium AcetateHCID 580439603,4,6,7,8,9-Hexahydropyrazino[1,2-a]indol-1(2H)-oneHCID 866842603-(2-Bromo-4-chloropyridin-3-yl)oxetan-3-ol

Product 1

HCID 866842612-(4-Chloro-3-(3-hydroxyoxetan-3-yl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-oneYield 42%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A 100 mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one 101e (190 mg, 1.0 mmol), 148a (795 mg, 3.0 mmol), CuI (95 mg, 0.5 mmol), DMEDA (88 mg, 1.0 mmol), KOAc(294 mg, 3.0 mmol), and 1,4-dioxane (50 ml). The system was evacuated and then refilled with N2. A reflux condenser was attached to the flask, and the reaction mixture was heated at 85° C. for 15 h. Then, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by flash column chromatography eluting with 2:1 petroleum ether/ethyl acetate to afford 148b as a yellow solid (156 mg, 42%). MS: [M+H]+ 374.2.

Workup

  1. customA 100 mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customThe system was evacuated
  3. additionrefilled with N2
  4. customA reflux condenser was attached to the flask
  5. temperatureThen, the mixture was cooled to room temperature
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe resulting residue was purified by flash column chromatography
  9. washeluting with 2:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-63dcce93e7c0426b8a15eebfac398ad9
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238655B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes