Sodium Carbonate → 4-(4-Amino-3-methanesulfonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1693118Notes

Reaction equation

HRID 1693118 reaction equation
C(O)(=O)C.[CH3:5][S:6]([C:9]1[CH:14]=[C:13]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:12]=[CH:11][C:10]=1[NH2:21])(=[O:8])=[O:7].[C:22]([O:26][C:27](=O)[O:28]C(C)(C)C)([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:22]([O:26][C:27]([N:18]1[CH2:17][CH2:16][CH:15]([C:13]2[CH:12]=[CH:11][C:10]([NH2:21])=[C:9]([S:6]([CH3:5])(=[O:8])=[O:7])[CH:14]=2)[CH2:20][CH2:19]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 86621317Acetic acid;2-methylsulfonyl-4-piperidin-4-ylaniline

Product 1

HCID 597599694-(4-Amino-3-methanesulfonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl esterYield 37.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methanesulfonyl-4-piperidin-4-yl-phenylamine; compound with acetic acid (1.5 g) in dichloromethane (30 ml) was added di-tert-butylcarbonate (1.15 g) and saturated aqueous sodium carbonate solution (10 ml). The reaction mixture was stirred at rt for 3 h and extracted with dichloromethane. The organic phases were dried and concentrated, and the residue was chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain the desired compound (0.64 g) as an off-white solid. MS (ISP): 355.1 (M+H)+

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic phases were dried
  3. concentrationconcentrated
  4. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-f9f3313f08d146edac148deb36682d33
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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