Piperazine → HCID 28917028, compound

HRID 1049036Notes

Reaction equation

HRID 1049036 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>O>[CH2:12]([NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH:13]([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 668999HCID 668999, compound

Product 1

HCID 28917028HCID 28917028, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A microwave vial was charged with 4-fluoro-N-isobutyl-benzenesulfonamide (1.0 g, 4.32 mmol), piperazine (1.86 g, 21.60 mmol) and water (20 mL) and heated at 150° C. for 1 hour using a microwave reactor. The solid from the reaction mixture was collected by filtration, washed with water and dried to give N-isobutyl-4-piperazin-1-yl-benzenesulfonamide (1.15 g, 90%). 1H NMR (300 MHz, CDCl3) δ 7.70 (d, J=9.0 Hz, 2H), 6.90 (d, J=9.0 Hz, 2H), 4.33 (t, J=6.5 Hz, 1H), 3.32-3.25 (m, 4H), 3.05-2.99 (m, 4H), 2.73 (t, J=6.6 Hz, 2H), 1.78-1.65 (m, 1H), 0.87 (d, J=6.7 Hz, 7H). LCMS (m/z, Method A) ES+ 298.2 [M+1]+.

Workup

  1. filtrationThe solid from the reaction mixture was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-023987e5e5e44e0a8fda38c4fefdd9c4
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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