Triethylamine → N-(1,4-dioxa-spiro[4.5]dec-8-yl)-4-fluoro-N-methyl-benzenesulfonamide

HRID 1663019Notes

Reaction equation

HRID 1663019 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([NH:11][CH3:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.CCN(CC)CC.[F:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]([CH3:12])[S:27]([C:24]3[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=3)(=[O:29])=[O:28])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 16786570N-methyl-1,4-dioxaspiro(4.5)decan-8-amine

Product 1

HCID 67435736N-(1,4-dioxa-spiro[4.5]dec-8-yl)-4-fluoro-N-methyl-benzenesulfonamideYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1,4-dioxa-spiro[4.5]dec-8-yl)-methyl-amine (1.5 g, 9 mmol), CH2Cl2 (50 mL), and Et3N (1.7 mL, 12 mmol) was stirred with 4-fluorobenzene sulfonyl chloride (1.7 g, 9 mmol) at room temperature. After 1 hour, the reaction mixture was concentrated and the residue purified by flash chromatography on silica gel to afford 2.1 g of N-(1,4-dioxa-spiro[4.5]dec-8-yl)-4-fluoro-N-methyl-benzenesulfonamide. Mass spectrometric data [M+H]+=330.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-03f67237ec284163a806f792a848a93c
Source dataset
uspto-grants-2011_10
Patent number
US08034826B2

Reaction notes

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