Diethyl Ether → {4-[1-(4-Bromo-phenyl)-2,3-dihydro-1H-indol-5-yloxy]-butyl}-diethyl-amine

HRID 1633672Notes

Reaction equation

HRID 1633672 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[BH3-]C#N.[Na+].CCOCC.[OH-].[Na+]>C(O)(C(F)(F)F)=O.O>[NH3:8].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 18679470{4-[1-(4-Bromo-phenyl)-1H-indol-5-yloxy]-butyl}-diethyl-amine

Product 2

HCID 222AmmoniaHCID 18679539{4-[1-(4-Bromo-phenyl)-2,3-dihydro-1H-indol-5-yloxy]-butyl}-diethyl-amineYield 76.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

104 mg (0.25 mmol) {4-[1-(4-Bromo-phenyl)-1H-indol-5-yloxy]-butyl}-diethyl-amine in 1 ml TFA were treated with 32 mg (0.5 mmol) NaCNBH3 at 0° C. for 5 min and 30 min at RT. Ether and water were added, followed by 2M NaOH. The inorganic phase was extracted with ether, the combined organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 19:1-1%sat.NH3 in MeOH yielded 40 mg (38%) {4-[1-(4-Bromo-phenyl)-2,3-dihydro-1H-indol-5-yloxy]-butyl}-diethyl-amine as light yellow waxy solid, MS: 417 (MH+, 1Br).

Workup

  1. extractionThe inorganic phase was extracted with ether
  2. washthe combined organic phases were washed with water
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-3f986c99150c4aa2a40db74674222a8b
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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