Acetic Acid → 6-Chloro-8-{4-[4-(1H-indole-4-yl)-1-piperazinyl]-1-piperidinyl}quinoline

HRID 2241980Notes

Reaction equation

HRID 2241980 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N:12]3[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]3)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[N:19]1([C:25]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:26]=2[CH:27]=[CH:28][NH:29]3)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl.ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([N:22]4[CH2:23][CH2:24][N:19]([C:25]5[CH:33]=[CH:32][CH:31]=[C:30]6[C:26]=5[CH:27]=[CH:28][NH:29]6)[CH2:20][CH2:21]4)[CH2:14][CH2:13]3)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 5049666Sodium triacetoxyborohydrideHCID 592048441-(6-Chloro-8-quinolinyl)-4-piperidinone

Product 1

HCID 120042826-Chloro-8-{4-[4-(1H-indole-4-yl)-1-piperazinyl]-1-piperidinyl}quinoline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1-(6-chloro-quinolin-8-yl)-piperidin-4-one (Step 1, 0.13 g) and of 4-piperazino-indole (commercially available, 0.100 g) in 15 mL CH2Cl2 in 10 mL of dichloroethane, was added 0.137 g of sodium triacetoxyborohydride and 0.1 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 and dried over magnesium sulfate. The product was filtered through 100 ml of silica gel using 100% Ethyl acetate, to give 0.070 g of the desired product. Mp: 224° C.; MS (ES) m/z (relative intensity): 447 (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. filtrationThe product was filtered through 100 ml of silica gel using 100% Ethyl acetate

Sources & evidence

ORD record
ord-e1cc4a6096f6499fb475cf1fcbfc5965
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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