Dimethylformamide → 5-[5-(Allyl-methyl-amino)-pentyl]-indole-1-carboxylic acid tert-butyl ester

HRID 1633645Notes

Reaction equation

HRID 1633645 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]OS(C)(=O)=O)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:27]([CH2:30][NH2:31])[CH:28]=C.[CH3:32]N(C=O)C>>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:31]([CH2:30][CH:27]=[CH2:28])[CH3:32])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 4437323-Buten-1-amineHCID 865855875-(5-Methanesulfonyloxy-pentyl)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 695479195-[5-(Allyl-methyl-amino)-pentyl]-indole-1-carboxylic acid tert-butyl esterYield 94%

Procedure

1.5 g (0.4 mmol) crude 5-(5-Methanesulfonyloxy-pentyl)-indole-1-carboxylic acid tert-butyl ester in 3 ml DMF were treated with 1.15 ml (12 mmol) N-allylmethylamine at 60° C. for 1 h. The solution was concentrated in vacuo and, the residue was dissolved in water and ether, 0.5M NaOH was added and the inorganic phase was extacted with ether. The combined organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel yielded 1.35 g (94%) 5-[5-(Allyl-methyl-amino)-pentyl]-indole-1-carboxylic acid tert-butyl ester as light yellow oil, MS: 357 (MH+).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. additionether, 0.5M NaOH was added
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-e15a2527680f4fa4b9330f515306ab54
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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