5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester → Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amine

HRID 1633677Notes

Reaction equation

HRID 1633677 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]([CH2:24][CH:25]=[CH2:26])[CH3:23])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:24]([N:22]([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][CH2:9][CH2:10]2)[CH3:23])[CH:25]=[CH2:26]

Participants

4

Reactant 1

HCID 695147375-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 21966572Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amineYield 98.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To 7.3 g (20.2) 5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 15 ml CH2Cl2, 10 ml trifluoro acetic acid were added at 0° C. The mixture was stirred at reflux for 3 h and was concentrated in vacuo. Water and 2M NaOH were added and the inorganic phase was extracted with ether. The combined organic phases were washed with water and dried over Na2SO4. Evaporation yielded 5.2 g (98%) Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amine as orange oil, MS: 261 (MH+)

Workup

  1. temperatureat reflux for 3 h
  2. concentrationwas concentrated in vacuo
  3. additionWater and 2M NaOH were added
  4. extractionthe inorganic phase was extracted with ether
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. customEvaporation

Sources & evidence

ORD record
ord-52b837f5bacd4dc9ab6ae46e5aa51e1b
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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