Water → HCID 18679562, compound

HRID 1633678Notes

Reaction equation

HRID 1633678 reaction equation
[CH2:1]([N:4]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH2:15][CH2:14]2)[CH3:5])[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+].[Cl:26][C:27]1[CH:32]=[CH:31][C:30](I)=[CH:29][CH:28]=1.O>CS(C)=O.[Cu]I.CCOCC>[CH2:1]([N:4]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:30]1[CH:31]=[CH:32][C:27]([Cl:26])=[CH:28][CH:29]=1)[CH:15]=[CH:14]2)[CH3:5])[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 125101-Chloro-4-iodobenzeneHCID 21966572Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amine

Product 1

HCID 18679562HCID 18679562, compoundYield 20.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
130 °C

Procedure

260 mg (1 mmol) Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amine in 2.5 ml DMSO were treated with 280 mg (2 mmol) powdered K2CO3 and 480 mg (2 mmol) 1-chloro-4-iodobenzene at 130° C. for 1 h. 19.1 mg (0.1 mmol) CuI were added and the mixture was stirred for additional 2 h at 130° C. At RT, water and ether were added, and the organic phase was washed with water, dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 19:1 yielded 75 mg (20%) Allyl-{4-[1-(4-chloro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-amine as orange oil, MS: 369 (MH+, 1Cl).

Workup

  1. customat 130° C.
  2. customfor 1 h
  3. washthe organic phase was washed with water
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-87400874405e4e1fab74b2a102e79f41
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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