Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → N-Methyl-N-tert-butoxycarbonyl-2-(3,4-dichlorophenyl)-2-(2-hydroxyethoxy)ethanamine

HRID 1840

Reaction equation

HRID 1840 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH3:18][N:19]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:20][CH:21]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=1)[O:22][CH2:23][CH2:24][O:25]C1CCCCO1>CO>[CH3:18][N:19]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:20][CH:21]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=1)[O:22][CH2:23][CH2:24][OH:25]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 19692483N-Methyl-N-tert-butoxycarbonyl-2-(3,4-dichlorophenyl)-2-[2-(tetrahydropyran-2-yloxy)ethoxy]ethanamine

Product 1

HCID 19692490N-Methyl-N-tert-butoxycarbonyl-2-(3,4-dichlorophenyl)-2-(2-hydroxyethoxy)ethanamineYield 100.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.56 g of pyridinium paratoluenesulfonate is added to a solution of 10 g of the compound obtained in EXAMPLE 8, step C), in 100 ml of MeOH and the reaction mixture is refluxed for 1 hour 15 minutes. It is concentrated under vacuum and the residue is taken up with ether, washed with water and with a buffer solution of pH 2, dried over MgSO4 and concentrated under vacuum to give 8.2 g of the expected product, which is used as such in the next step.

Workup

  1. temperaturethe reaction mixture is refluxed for 1 hour 15 minutes
  2. concentrationIt is concentrated under vacuum
  3. washwashed with water and with a buffer solution of pH 2
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c7a3ca41e01d4efebb1bd0e9b36a8939
Source dataset
uspto-grants-1998_03
Patent number
US05726313

Linked notes

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