Acetic Acid → 5-[4-(Tert-butoxycarbonyl)piperazin-1-ylmethyl]indole

HRID 20975

Reaction equation

HRID 20975 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)=O.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([CH2:1][C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][CH:7]=[CH:6]3)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 589040Indole-5-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 684899345-[4-(Tert-butoxycarbonyl)piperazin-1-ylmethyl]indoleYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

5-Formylindole (500 mg, 3.44 mmol) was dissolved in acetonitrile (10 mL), and the solution was added with 1-(tert-butoxycarbonyl)piperazine (961 mg, 5.16 mmol), acetic acid (3.90 mL, 68.1 mmol) and sodium triacetoxyborohydride (3.65 g, 17.2 mmol) little by little, followed by stirring at room temperature for 2 hours. The reaction mixture was added with water and sodium carbonate to adjust the pH to 9, followed by extracting with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (hexane/ethyl acetate=19/1, 7/3, 1/1) to obtain 5-[4-(tert-butoxycarbonyl)piperazin-1-ylmethyl]indole (505 mg, yield 47%).

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash column chromatography (hexane/ethyl acetate=19/1, 7/3, 1/1)

Sources & evidence

ORD record
ord-40825bde11ad4d73a783930ebca6be83
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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