4-Fluorobenzenesulfonyl chloride → HCID 18374698, compound

HRID 2301190Notes

Reaction equation

HRID 2301190 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(Cl)Cl.C(OCC)C>[F:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 18374698HCID 18374698, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (DIEA, 0.7 mL, 2 mmol) was added to a solution of 4-(aminomethyl)-1-tert-butoxycarbonylpiperidine (200 mg, 0.93 mmol) in 5 mL of CH2Cl2 under nitrogen. (4-fluorophenyl)sulfonyl chloride (195 mg, 1 mmol) was then added, and the reaction mixture was stirred at room temperature for 30 min. The solution was diluted with diethyl ether, washed with 1N HCl, 1N NaOH, and brine, and then dried over MgSO4. The solution was then concentrated to afford 284 mg (82% yield) of the title compound, which could be purified by recrystallization from diethyl ether. 1H NMR (300 MHz, CDCl3). δ 1.00-1.13 (m, 1H), 1.42 (s, 9H), 1.61-1.70 (m, 3H), 2.58-2.70 (m, 2H), 2.80-2.84 (m, 2H), 4.02-4.16 (m, 2H), 4.46-4.52 (m, 1H), 7.17-7.22 (m, 2H), 7.82-7.90 (m, 2H).

Workup

  1. washwashed with 1N HCl, 1N NaOH, and brine
  2. dry with materialdried over MgSO4
  3. concentrationThe solution was then concentrated

Sources & evidence

ORD record
ord-f34005a60de24e8eafeaeed2b535f7cb
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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