Trifluoroacetic acid → N-[3-amino-3-(4-chlorophenyl)propyl]methanesulfonamide

HRID 423123Notes

Reaction equation

HRID 423123 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:23]C(=O)OC(C)(C)C)[CH2:16][CH2:17][NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:11][CH:10]=1>>[NH2:23][CH:15]([C:12]1[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=1)[CH2:16][CH2:17][NH:18][S:19]([CH3:22])(=[O:21])=[O:20]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57750293Tert-butyl 1-(4-chlorophenyl)-3-(methylsulfonamido)propylcarbamate2×

Product 1

HCID 57750326N-[3-amino-3-(4-chlorophenyl)propyl]methanesulfonamideYield 56.7%

Conditions

Temperature
20 °C

Procedure

TFA (4 mL) was added to tert-butyl 1-(4-chlorophenyl)-3-(methylsulfonamido)propylcarbamate (Intermediate 115) (275 mg, 0.76 mmol) and stirred at 20° C. for 2 hours. The reaction was vacuumed to dryness. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford N-(3-amino-3-(4-chlorophenyl)propyl)methanesulfonamide (113 mg, 56.7%) as a colourless gum.

Workup

  1. customThe crude product was purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customwere evaporated to dryness

Sources & evidence

ORD record
ord-b8a7f386d3a9466f8c20fb4b0c6f4d6e
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

Loading…