Tetrahydrofuran → HCID 68872252, compound

HRID 1725676Notes

Reaction equation

HRID 1725676 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].C([N:17]([CH:20]([CH3:22])C)[CH2:18][CH3:19])(C)C.C[N:24]1CCC(N)CC1.O1[CH2:35][CH2:34]CC1>>[CH3:34][CH:35]1[CH2:19][CH2:18][N:17]([NH:24][S:2]([C:5]2[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:9][CH:10]=2)(=[O:4])=[O:3])[CH2:20][CH2:22]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 84763-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidine

Product 1

HCID 68872252HCID 68872252, compound

Procedure

To a solution of 3-chlorosulfonylnitrobenzene (45) (2.21 g, 10 mmol) in tetrahydrofuran (100 mL) at 0° C. were added diisopropylethyl amine (1.93 mL, 15 mmol) followed by N-methyl-4-aminopiperidine (46) (1.36 g, 12 mmol) and then the reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched with water (50 mL), stirred for 30 minutes and the tetrahydrofuran layer was separated. The organic solution was concentrated under reduced pressure. The resulting residue was taken in dichloromethane (200 mL), washed with aqueous solution of sodium bicarbonate (2×100 mL) and then brine. The organic layer was dried over anhydrous sodium sulfate and solvent was removed under reduced pressure to afford the desired product, 3-(N-4-methylpiperidin-1-yl)aminosulfonylnitrobenzene (47). LCMS: purity: 93%; MS (m/e): 300 (MH+).

Workup

  1. customThe reaction was quenched with water (50 mL)
  2. stirringstirred for 30 minutes
  3. customthe tetrahydrofuran layer was separated
  4. concentrationThe organic solution was concentrated under reduced pressure
  5. washwashed with aqueous solution of sodium bicarbonate (2×100 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate and solvent
  7. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-49fdd58a8b534c5aa90b96997fa570b7
Source dataset
uspto-grants-2009_02
Patent number
US07491732B2

Reaction notes

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