Sodium Hydroxide → Diethyl-[4-(1H-indol-5-yloxy)-butyl]-amine

HRID 1633628Notes

Reaction equation

HRID 1633628 reaction equation
C(OC([N:8]1[C:16]2[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]=2)[CH:10]=[CH:9]1)=O)(C)(C)C.[OH-].[Na+]>CCO>[CH2:25]([N:22]([CH2:23][CH3:24])[CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][CH:9]=[CH:10]2)[CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 695488375-(4-Diethylamino-butoxy)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 18679455Diethyl-[4-(1H-indol-5-yloxy)-butyl]-amineYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.9 g (10.8 mmol) 5-(4-Diethylamino-butoxy)-indole-1-carboxylic acid tert-butyl ester in 4 ml EtOH were treated with 0.4 ml halfconc. NaOH at 60° C. for 2 h. The suspension was concentrated in vacuo and the residue dissolved in EtOAc and water. The organic phase was washed with water and dried over Na2SO4. Evaporation yielded 2.7 g (96%) Diethyl-[4-(1H-indol-5-yloxy)-butyl]-amine as brown oil, MS: 261 (MH+).

Workup

  1. concentrationThe suspension was concentrated in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. customEvaporation

Sources & evidence

ORD record
ord-a70007d2915c45308cae53b33c0735f6
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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