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Potassium Carbonate → N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline

HRID 45720
Notes
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Reaction equation

HRID 45720 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[C:13]([Cl:19])[CH:14]=[C:15]([Cl:18])[CH:16]=3)[CH2:11][N:10]([CH3:20])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[N:21]([CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][NH2:35])=[N+:22]=[N-:23].N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[N:21]([CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][NH:35][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[C:17]3[C:12](=[C:13]([Cl:19])[CH:14]=[C:15]([Cl:18])[CH:16]=3)[CH2:11][N:10]([CH3:20])[CH2:9]2)[CH:3]=1)=[N+:22]=[N-:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 27352801-Amino-11-azido-3,6,9-trioxaundecaneHCID 223869034-(3-Bromophenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline2×

Product 1

HCID 86699380N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

Into a 10-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-(3-bromophenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline (intermediate 1.4) (400 mg, 1.08 mmol, 1.00 equiv) in DMSO (6 mL), 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethanamine (236.11 mg, 1.08 mmol, 1.00 equiv), (S)-pyrrolidine-2-carboxylic acid (24.79 mg, 0.21 mmol, 0.20 equiv), copper(I) iodide (20.48 mg, 0.11 mmol, 0.10 equiv) and potassium carbonate (223.18 mg, 1.62 mmol, 1.50 equiv). The resulting solution was stirred at 90° C. in an oil bath and the reaction progress was monitored by LCMS. After stirring overnight the reaction mixture was cooled with a water/ice bath and then diluted with ice water. The resulting solution was extracted with 3×30 mL of ethyl acetate and the organic extracts were combined and washed with 2×20 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (2:1). This resulted in 130 mg (24%) of N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenamine as yellow oil.

Workup

  1. customInto a 10-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringAfter stirring overnight the reaction mixture
  4. temperaturewas cooled with a water/ice bath
  5. extractionThe resulting solution was extracted with 3×30 mL of ethyl acetate
  6. washwashed with 2×20 mL of brine
  7. dry with materialThe mixture was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThis resulted in 130 mg (24%) of N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenamine as yellow oil

Sources & evidence

ORD record
ord-f592563881f74c998d5c370348003aed
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541448B2

Reaction notes

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