Triethylamine → HCID 22052648, compound

HRID 1403715Notes

Reaction equation

HRID 1403715 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:24][S:25]([N:12]1[CH2:11][CH2:10][CH:9]([O:8][C:7]2[CH:15]=[CH:16][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:14][CH2:13]1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 219186534-(4-Nitrophenoxy)piperidine

Product 1

HCID 22052648HCID 22052648, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(4-nitro-phenoxy)-piperidine (7.80 g, 35.1 mmol) and triethylamine (7.77 mL, 56.2 mmol) in DCM (100 mL) at 0° C. was treated dropwise with methanesulfonyl chloride (3.26 mL, 42.1 mmol) and stirred cold for 1 hour. The mixture was diluted with DCM, washed with 1M HCl, a saturated NaHCO3 solution, water and brine, dried over Na2SO4 and concentrated under vacuum to leave the title compound (9.10 g, 86% yield) as a yellow/orange solid. 1H NMR (300 MHz, CDCl3) δ 8.21 (d, J=9.2 Hz, 2H), 6.97 (d, J=9.2 Hz, 2H), 4.68 (m, 1H), 3.39 (m, 4H), 2.84 (s, 3H), 2.05 (m, 4H). LCMS (m/z, Method A) ES+ 301.0 [M+1]+.

Workup

  1. washwashed with 1M HCl
  2. dry with materiala saturated NaHCO3 solution, water and brine, dried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4762b0c892814de9969d6fa0d9dcfea4
Source dataset
uspto-grants-2014_12
Patent number
US08912219B2

Reaction notes

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