4-Fluorobenzenesulfonyl chloride → HCID 23553541, compound

HRID 1634743Notes

Reaction equation

HRID 1634743 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].F[C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C([N:30](C(C)C)CC)(C)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([S:23]([C:20]2[CH:21]=[CH:22][C:17]([NH2:30])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 23553541HCID 23553541, compoundYield 111%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of [piperidin-4-ylmethyl]-carbamic acid t-butyl ester (4.28 g, 20 mmol), 4-fluorobenzenesulfonyl chloride (3.89 g, 20 mmol), and diisopropylethyl amine (3.5 mL, 20 mmol) in 50 mL of CH2Cl2 was stirred at ambient temperature overnight. The reaction mixture was diluted to twice its volume with CH2Cl2 and washed with 1N HCl, brine and dried (Na2SO4). The solvent was evaporated in vacuo to give 8.2 g of product as a white solid.

Workup

  1. washwashed with 1N HCl, brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e13def468fec4b3aaaacec98a5c0d67d
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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