Piperidine → HCID 10458941, compound

HRID 1827558Notes

Reaction equation

HRID 1827558 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31]C3CCCCO3)[CH:26]=2)[S:12]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])(=[O:14])=[O:13])=[CH:7][CH:6]=1.[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>O1CCCC1.C(OCC)(=O)C>[OH:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[CH2:24][N:11]([C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH2:2][N:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:10][CH:9]=1)[S:12]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=1[CH3:23])(=[O:14])=[O:13]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 22137407HCID 22137407, compound

Product 1

HCID 10458941HCID 10458941, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[4-(2-bromo-ethoxy)-phenyl]-2,4,6-trimethyl-N-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide (0.070 g, 0.12 mmol) in 2 mL tetrahydrofuran was added piperidine (0.12 mL, 1.21 mmol). The reaction mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted to a volume of 30 mL with ethyl acetate and was washed with saturated aqueous sodium bicarbonate (2×15 mL) and saturated aqueous sodium chloride (1×15 mL). The organic layer was dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography (5% methanol/methylene chloride) afforded 0.010 g of an oil. The oil was further purified by preparative TLC (0.5 mm silica gel layer, eluting with 10% methanol/methylene chloride) to afford 0.003 g of the title compound. MS 509.2 (M+1)+

Workup

  1. washwas washed with saturated aqueous sodium bicarbonate (2×15 mL) and saturated aqueous sodium chloride (1×15 mL)
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-298563b5b412478db86f8641af65087d
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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