1-Acetylpiperazine → HCID 59331477, compound

HRID 1882001Notes

Reaction equation

HRID 1882001 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:19]2[NH:23][C:22]([C:24]3[CH:29]=[C:28]([CH:30]=O)[CH:27]=[CH:26][N:25]=3)=[CH:21][CH:20]=2)[CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:32]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)(=[O:34])[CH3:33].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[C:32]([N:35]1[CH2:40][CH2:39][N:38]([CH2:30][C:28]2[CH:27]=[CH:26][N:25]=[C:24]([C:22]3[NH:23][C:19]([CH:11]([C:8]4[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=4)[CH2:12][CH:13]4[CH2:14][CH2:15][O:16][CH2:17][CH2:18]4)=[CH:20][CH:21]=3)[CH:29]=2)[CH2:37][CH2:36]1)(=[O:34])[CH3:33]

Participants

6

Reactant 3

HCID 837951-AcetylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 59331432HCID 59331432, compound

Product 1

HCID 59331477HCID 59331477, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(5-{1-[4-(methylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridine-4-carbaldehyde (170 mg) in 1,2-dichloroethane (5 mL) was added 1-acetylpiperazine (115 mg), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added sodium triacetoxyborohydride (250 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to basic silica gel column chromatography, and the title compound (180 mg, yield 85%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-methanol (19:1, volume ratio). MS: 551 (MH+).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. washwashed with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d9a7ebddf3d044cf87a4d9a8f1a0b773
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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