Ammonium Hydroxide → 1-[4-(Ethylsulfonyl)phenyl]methanamine

HRID 1777813Notes

Reaction equation

HRID 1777813 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[NH4+:15]>CO>[CH2:12]([S:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH2:15])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH3:13]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 672188351-(Bromomethyl)-4-(ethanesulfonyl)benzene

Product 1

HCID 179666261-[4-(Ethylsulfonyl)phenyl]methanamineYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(bromomethyl)-4-(ethylsulfonyl)benzene (6.62 g, 25.2 mmol) in MeOH (30 mL) was added 28% aqueous ammonium hydroxide solution (30 mL). The mixture was stirred at rt overnight. The mixture was then concentrated under reduced pressure. The residue was purified by basic preparative HPLC separation to afford (4-(ethylsulfonyl)phenyl)methanamine (1.5 g, 30%) as a yellow solid. LC-MS tR=1.747 min in 0-30CD—3 min chromatography (Durashell C18, 2.1*30 mm, 3 um), MS (ESI) m/z 200.0 [M+H]+ and 399.0 [2M+H]+. 1H NMR (CDCl3, 400 MHz): δ 7.85 (d, J=8.0 Hz, 2H), 7.53 (d, J=8.0 Hz, 2H), 3.98 (s, 2H), 3.10 (q, J=7.6 Hz, 2H), 1.26 (t, J=7.6 Hz, 3H). Preparative Basic HPLC Method mobile phase A: water with 0.05% NH3H2O solution; mobile phase B: MeCN; flow rate: 30 mL/min; detection: UV 220 nm/254 nm; column: Synergi 200 mm×25 mm×5 μm; column temperature: 30° C.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customThe residue was purified by basic preparative HPLC separation

Sources & evidence

ORD record
ord-e1698380f64c4154a5313e8634b4e576
Source dataset
uspto-grants-2016_02
Patent number
US09266886B2

Reaction notes

Loading…