Trifluoroacetic acid → HCID 23498812, compound

HRID 1836133Notes

Reaction equation

HRID 1836133 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:27])[CH2:15][CH2:16][C:17]2[C:25]3[C:24](=[O:26])[CH2:23][CH2:22][CH2:21][C:20]=3[NH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[O:27]=[C:14]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH2:15][CH2:16][C:17]1[C:25]2[C:24](=[O:26])[CH2:23][CH2:22][CH2:21][C:20]=2[NH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69839741HCID 69839741, compound

Product 1

HCID 23498812HCID 23498812, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[3-(4-Oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionyl]-piperazine-1-carboxylic acid tert-butyl ester (37.5mg, 0.1 mmol) was added to 3 ml of dichloromethane at 0° C. followed by the addition of 1 ml of 20% trifluoroacetic acid. The reaction mixture was stirred at room temperature for 8 hours. The reaction solution was rotary evaporated and diluted with 1,4-dioxane. The reaction solution was concentrated at 30° C. till dryness then purified by flash chromatography and eluting with (chloroform: methanol: ammonia 20/1/0.1, 15/1/0.1) to provide 3-(3-oxo-3-piperazin-1-yl-propyl)-1,5,6,7-tetrahydro-indol-4-one.

Workup

  1. customThe reaction solution was rotary evaporated
  2. additiondiluted with 1,4-dioxane
  3. concentrationThe reaction solution was concentrated at 30° C. till dryness
  4. customthen purified by flash chromatography
  5. washeluting with (chloroform: methanol: ammonia 20/1/0.1, 15/1/0.1)

Sources & evidence

ORD record
ord-e993f75efe20444d8f938f081400c915
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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