4-Methoxybenzylamine → HCID 3794176, compound

HRID 2252058Notes

Reaction equation

HRID 2252058 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[CH:11]([S:14](Cl)(=[O:16])=[O:15])([CH3:13])[CH3:12]>ClCCl>[CH:11]([S:14]([NH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:16])=[O:15])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 824082-Propanesulfonyl chloride

Product 1

HCID 3794176HCID 3794176, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 4-methoxy-benzylamine (11.7 m, 89.5 mmol) to a solution of isopropyl sulfonyl chloride (5.0 mL, 44.74 mmol) in dichloromethane (100 mL) and stir for 18 hours at ambient temperature. Wash solution with 1 N hydrochloric acid (3×100 mL), dry with magnesium sulfate and concentrate. Purify on silica gel with hexane/ethyl acetate mixtures to give 4.73 g (43%) of the title compound as a white solid. MS(ES−): m/z=242.1 (M−H)−

Workup

  1. dry with materialWash solution with 1 N hydrochloric acid (3×100 mL), dry with magnesium sulfate
  2. concentrationconcentrate
  3. customPurify on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-26b0528ec85145e785582be77a447d5b
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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