Water → Allyl-[5-(1H-indol-5-yl)-pentyl]-methyl-amine

HRID 1633646Notes

Reaction equation

HRID 1633646 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:24][CH:25]=[CH2:26])[CH3:23])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=O)(C)(C)C.O.[OH-].[Na+]>C(O)C>[CH2:24]([N:22]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][CH:9]=[CH:10]2)[CH3:23])[CH:25]=[CH2:26]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 695479195-[5-(Allyl-methyl-amino)-pentyl]-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 18679431Allyl-[5-(1H-indol-5-yl)-pentyl]-methyl-amineYield 100.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To 1.3 g (3.5 mmol) 5-[5-(Allyl-methyl-amino)-pentyl]-indole-1-carboxylic acid tert-butyl ester in 20 ml ethanol were added 1.5 ml water and 3 ml conc. NaOH, and stirred at 60° C. for 1.5 h. The slurry was concentrated and dissolved in ether/water. The organic layer was washed with water and dried over Na2SO4 and evaporated to yield 900 mg (quantitative) Allyl-[5-(1H-indol-5-yl)-pentyl]-methyl-amine as light yellow oil, MS: 257 (MH+).

Workup

  1. concentrationThe slurry was concentrated
  2. dissolutiondissolved in ether/water
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-e9477ea355954d338c169555cac28ba8
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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