Diethylamine → 5-(4-Diethylamino-butoxy)-indole-1-carboxylic acid tert-butyl ester

HRID 1633627Notes

Reaction equation

HRID 1633627 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21]Br)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([NH:25][CH2:26][CH3:27])[CH3:24]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:25]([CH2:26][CH3:27])[CH2:23][CH3:24])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 695484135-(4-Bromo-butoxy)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 695488375-(4-Diethylamino-butoxy)-indole-1-carboxylic acid tert-butyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.8 g (13 mmol) 5-(4-Bromo-butoxy)-indole-1-carboxylic acid tert-butyl ester in 5 ml DMF were treated with 5 ml (48.1 mmol) diethylamine at 50° C. for 5 h. The solution was concentrated and extracted with ether and water. The combined organic phases were dried over Na2SO4 to yield 3.95 g (85%) 5-(4-Diethylamino-butoxy)-indole-1-carboxylic acid tert-butyl ester as yellow oil, MS: 361 (MH+).

Workup

  1. concentrationThe solution was concentrated
  2. extractionextracted with ether and water
  3. dry with materialThe combined organic phases were dried over Na2SO4

Sources & evidence

ORD record
ord-3783e024a9a04505839fc1a4848767e2
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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