1,3-Propanediamine → N-(3-aminopropyl)-4-(4-fluorophenoxy)benzenesulfonamide

HRID 2301726Notes

Reaction equation

HRID 2301726 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].[F:6][C:7]1[CH:23]=[CH:22][C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1>ClCCl>[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][S:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][C:10]2[CH:22]=[CH:23][C:7]([F:6])=[CH:8][CH:9]=2)=[CH:13][CH:14]=1)(=[O:19])=[O:20]

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 27827574-(4-Fluorophenoxy)benzenesulphonyl chloride

Product 1

HCID 22592864N-(3-aminopropyl)-4-(4-fluorophenoxy)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1,3-diaminopropane (6.7 mL) in 100 mL of dichloromethane at −10° C. was slowly added over a 2 hour period a solution of 4-(4-fluorophenoxy)benzenesulfonyl chloride (5.7 g, 20 mmol) in 50 mL of dichloromethane. The reaction was stirred for 15 minutes after the addition was complete, and then partitioned between ethyl acetate and water. The resulting emulsion was cleared by addition of dichloromethane, and the organic layer was separated. The aqueous layer was extracted with dichloromethane and the combined organic layers were extracted with 0.5 N aq. sodium bisulfate. The aqueous phase was brought to pH 8 with sodium bicarbonate and then extracted with dichloromethane (3×100 mL). The combined organic layers were dried over sodium sulfate and concentrated to a volume of about 50 mL. Addition of hexane resulting in formation of a precipitate, which was collected by filtration to provide N-(3-aminopropyl)-4-(4-fluorophenoxy)benzenesulfonamide (4.27 g) as a white solid: mp 184° C. (softens), 237° C. (melts) 1H NMR (300 MHz, DMSO-d6): δ 7.84 (d, J=9 Hz, 2H), 7.38-7.21 (m, 4H), 7.12 (d, J=9 Hz, 2H), 3.6-3.2 (br s, 3H), 2.80 (dd, J=7, 7 Hz, 2H), 2.77 (dd, J=7, 7 Hz, 2H), 1.72-1.60 (m, 2H).

Workup

  1. additionafter the addition
  2. custompartitioned between ethyl acetate and water
  3. additionThe resulting emulsion was cleared by addition of dichloromethane
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. extractionthe combined organic layers were extracted with 0.5 N aq. sodium bisulfate
  7. extractionextracted with dichloromethane (3×100 mL)
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. concentrationconcentrated to a volume of about 50 mL
  10. additionAddition of hexane resulting in formation of a precipitate, which
  11. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-f7251a974bcc42e1a7a1967431338c0d
Source dataset
uspto-grants-2002_12
Patent number
US06500948B1

Reaction notes

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