4-Methylpiperidine → HCID 10478369, compound

HRID 1827596Notes

Reaction equation

HRID 1827596 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH:27]=[O:28])=[CH:21][CH:20]=1)[S:7]([C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])(=[O:9])=[O:8].[CH3:32][CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]([C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH2:27][N:36]2[CH2:37][CH2:38][CH:33]([CH3:32])[CH2:34][CH2:35]2)=[CH:23][CH:24]=1)[S:7]([C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])(=[O:9])=[O:8].[OH:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]([C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH2:27][OH:28])=[CH:23][CH:24]=1)[S:7]([C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])(=[O:9])=[O:8]

Participants

7

Reactant 4

HCID 693814-MethylpiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22137280HCID 22137280, compound

Product 2

HCID 10478369HCID 10478369, compoundHCID 10481802HCID 10481802, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3-hydroxy-benzyl)-2,4,6-trimethyl-N-[4-(3-oxo-propyl)-phenyl]-benzenesulfonamide (0.040 g, 0.09 mmol) in 2 mL methylene chloride was added 4-methylpiperidine (0.015 g, 0.15 mmol) and NaB(OAc)3H (0.047 g, 0.22 mmol). The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the aqueous solution was washed with methylene chloride. The organic layer was dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography (10% methanol/methylene chloride) followed by further medium-pressure chromatography (40% ethyl acetate/hexanes) afforded a mixture comprising 0.008 g of N-(3-hydroxy-benzyl)-2,4,6-trimethyl-N-{4-[3-(4-methyl-piperidin-1-yl)-propyl]-phenyl}-benzenesulfonamide and 0.017 g of N-(3-hydroxy-benzyl)-N-[4-(3-hydroxy-propyl)phenyl]-2,4,6-trimethyl-benzenesulfonamide. MS 440.2 (M+1)+

Workup

  1. washthe aqueous solution was washed with methylene chloride
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b6beab8fc8b14935947c9cd0e11b9e64
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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