Water → {4-[1-(4-Bromo-benzyl)-1H-indol-5-yloxy]-butyl}-diethyl-amine

HRID 1633633Notes

Reaction equation

HRID 1633633 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[CH3:2].[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1.CCOCC.O>CN(C=O)C>[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:14]2[C:15]3[C:11](=[CH:10][C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:18][CH3:19])=[CH:17][CH:16]=3)[CH:12]=[CH:13]2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 685274-Bromobenzyl bromideHCID 18679455Diethyl-[4-(1H-indol-5-yloxy)-butyl]-amine

Product 1

HCID 18679552{4-[1-(4-Bromo-benzyl)-1H-indol-5-yloxy]-butyl}-diethyl-amineYield 53.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

130 mg (0.5 mmol) Diethyl-[4-(1H-indol-5-yloxy)-butyl]-amine in 1 ml DMF were treated with 67 mg (0.6 mmol) potassium tert. butylate and 150 mg (0.6 mmol) 4-bromobenzylbromide at 45° C. for 1 h. Ether and water were added and the organic phase was washed with water and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2: MeOH 9:1 yielded 115 mg (53%) {4-[1-(4-Bromo-benzyl)-1H-indol-5-yloxy]-butyl}-diethyl-amine as colorless oil, MS: 429 (MH+, 1Br).

Workup

  1. washthe organic phase was washed with water
  2. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-a2e02a3dd96949689dd92b83c0ef961b
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

Loading…