Triethylamine → HCID 68473866, compound

HRID 1466486Notes

Reaction equation

HRID 1466486 reaction equation
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:20]Br)=[CH:14][C:15]=2[N+:17]([O-:19])=[O:18])[C:10]([Br:22])=[C:9]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.[O:36]=[C:37]1[CH2:42][NH:41][CH2:40][CH2:39][NH:38]1.[NH4+].[Cl-]>C(Cl)Cl>[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:20][N:41]3[CH2:40][CH2:39][NH:38][C:37](=[O:36])[CH2:42]3)=[CH:14][C:15]=2[N+:17]([O-:19])=[O:18])[C:10]([Br:22])=[C:9]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 231360Piperazin-2-oneHCID 68472286HCID 68472286, compound

Product 1

HCID 68473866HCID 68473866, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-BOC-3-bromo-5-bromomethyl-7-nitro-2-phenyl-indole prepared in Step B (1.0 g, 2 mmol) was dissolved in DCM (10 mL). Et3N (560 uL, 4 mmol) was added, 2-oxo-piperazine (300 mg, 3 mmol) was added, and the mixture was stirred for 12 h at room temperature. After completion of the reaction, saturated aqueous NH4Cl solution was added, and the reaction mixture was extracted with DCM. After drying, the solvent was removed under reduced pressure. The residue was purified by column chromatography to give the title compound (825 mg, Yield 78%).

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted with DCM
  3. customAfter drying
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ba89f6e9517e4b969840f319ce5ed92e
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

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