Trifluoroacetic acid → Allyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amine

HRID 2212542Notes

Reaction equation

HRID 2212542 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)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[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][CH2:9][CH2:10]2)[CH3:23])[CH:25]=[CH2:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 695141225-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 21966638Allyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.45 g (6.8 mmol) 5-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 5 ml CH2Cl2 were treated with 4 ml TFA at 0° C. The solution was stirred at RT for 0.5 h, and at 40° C. for 1 h. The solution was concentrated and the residue was dissolved in ether and water. 2M NaOH was added and the inorganic phase was extracted with ether. The combined organic phases were washed with water and dried over Na2SO4 to yield 1.65 g (94%) Allyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amine as light yellow oil, MS: 259 (MH+).

Workup

  1. waitat 40° C. for 1 h
  2. concentrationThe solution was concentrated
  3. dissolutionthe residue was dissolved in ether
  4. addition2M NaOH was added
  5. extractionthe inorganic phase was extracted with ether
  6. washThe combined organic phases were washed with water
  7. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-0de85bcf4ef44040929693bcb65d407d
Source dataset
uspto-grants-2006_09
Patent number
US07102007B2

Reaction notes

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