Sodium Carbonate → 1-(4-1H-indolyl)-4-[3,3-bis-(2-pyridyl)propyl]piperazine

HRID 2181640Notes

Reaction equation

HRID 2181640 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH2:8][CH:9]=O.[NH:17]1[C:25]2[C:20](=[C:21]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.ClCCCl.C(O)(=O)C>[NH:17]1[C:25]2[C:20](=[C:21]([N:26]3[CH2:31][CH2:30][N:29]([CH2:9][CH2:8][CH:7]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=4)[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:28][CH2:27]3)[CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 5049666Sodium triacetoxyborohydrideHCID 224821053,3-Bis-(2-pyridyl)propionaldehyde

Product 1

HCID 224821081-(4-1H-indolyl)-4-[3,3-bis-(2-pyridyl)propyl]piperazineYield 13%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 1.15 g of Compound 16B, 1.2 g of 1-(4-indolyl)piperazine (prepared as described in EP 138,280), 1.24 mL of acetic acid, 1.71 g of sodium triacetoxyborohydride and 85 mL of 1,2-dichloroethane was stirred at room temperature for 24 h. Afterwards it was diluted with water and alkalinized with sodium carbonate. The organic layer was dried on sodium sulphate and evaporated to dryness affording 1.53 g of crude, which was purified by flash chromatography (ethyl acetate-2.2 N methanolic ammonia, gradient from 9.4:0.6 to 9.2:0.8) affording 0.28 g (13%) of the title product as an oil.

Workup

  1. customThe organic layer was dried on sodium sulphate
  2. customevaporated to dryness
  3. customaffording 1.53 g of crude, which
  4. customwas purified by flash chromatography (ethyl acetate-2.2 N methanolic ammonia, gradient from 9.4:0.6 to 9.2:0.8)

Sources & evidence

ORD record
ord-db0f40ea5c0a4605b13a3af8ae4a87b1
Source dataset
uspto-grants-2005_05
Patent number
US06894052B1

Reaction notes

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