Propylamine → 1-Propanamine, N-[2-[3-fluoro-5-(methylsulfonyl)phenoxy]ethyl]-

HRID 1468640Notes

Reaction equation

HRID 1468640 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[C:7]([F:15])[CH:6]=1.[CH2:16]([NH2:19])[CH2:17][CH3:18]>C(O)C>[F:15][C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=1)[O:4][CH2:3][CH2:2][NH:19][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 86717739HCID 86717739, compound

Product 1

HCID 709804851-Propanamine, N-[2-[3-fluoro-5-(methylsulfonyl)phenoxy]ethyl]-Yield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene (2.65 g, 8.9 mmol) and propan-1-amine (5.24 ml, 63.7 mmol) in ethanol (32 ml) was divided into 3 aliquots which were each heated under microwave radiation at 120° C. for 30 min. The reaction mixtures were cooled to room temperature, filtrated and pooled before the volatiles were evaporated. Purification by flash column chromatography (ethyl acetate/methanol, 1:0 to 1:1) gave the title compound (2.14 g, 87%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 191° C. MS m/z (relative intensity, 70 eV) 275 (M+, 2), 246 (32), 73 (5), 72 (bp), 56 (11).

Workup

  1. customThe reaction mixtures
  2. temperaturewere cooled to room temperature
  3. filtrationfiltrated
  4. customwere evaporated
  5. customPurification by flash column chromatography (ethyl acetate/methanol, 1:0 to 1:1)

Sources & evidence

ORD record
ord-f626e3d81ac14e19bc57b23a26299624
Source dataset
uspto-grants-2015_04
Patent number
US09006227B2

Reaction notes

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