Acetic Acid → 8-{4-[4-(1H-indole-4-yl)-1-piperazinyl]-1-piperidinyl}quinoline

HRID 2241971Notes

Reaction equation

HRID 2241971 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N:11]2[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)[CH:4]=[CH:3][CH:2]=1.[N:18]1([C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH:26]=[CH:27][NH:28]3)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[NH:28]1[C:29]2[C:25](=[C:24]([N:18]3[CH2:23][CH2:22][N:21]([CH:14]4[CH2:15][CH2:16][N:11]([C:9]5[CH:8]=[CH:7][CH:6]=[C:5]6[C:10]=5[N:1]=[CH:2][CH:3]=[CH:4]6)[CH2:12][CH2:13]4)[CH2:20][CH2:19]3)[CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:27]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 5049666Sodium triacetoxyborohydrideHCID 592048421-Quinolin-8-yl-piperidin-4-one

Product 1

HCID 120042838-{4-[4-(1H-indole-4-yl)-1-piperazinyl]-1-piperidinyl}quinolineYield 40.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.270 g of 1-quinolin-8-yl-piperidin-4-one (Example A, Step 6, above) and 0.240 g of 4-piperazino-indole (commercially available) in 15 mL CH2Cl2 was added 0.327 g of sodium triacetoxyborohydride and 0.2 mL acetic acid. The reaction was stirred at room temperature overnight. It was quenched with 1N NaOH, and the product was extracted with CH2Cl2. The organic phase was washed with water, dried over magnesium sulfate and evaporated. The product crystallized to give 0.200 g of the desired product. Mp: 256° C.; MS (ES) m/z (relative intensity): 412 (M++−H, 100).

Workup

  1. customIt was quenched with 1N NaOH
  2. extractionthe product was extracted with CH2Cl2
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe product crystallized

Sources & evidence

ORD record
ord-93c30f2efedf4440930022e387a7a6f5
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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