Diisopropylethylamine → HCID 49458657, compound

HRID 1523764Notes

Reaction equation

HRID 1523764 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[C:12]([NH:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:14])[CH3:13].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:19]1[CH2:20][CH2:21][CH:16]([NH:15][C:12](=[O:14])[CH3:13])[CH2:17][CH2:18]1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5204032-Bromobenzenesulfonyl chlorideHCID 14451564-Acetamidopiperidine

Product 1

HCID 49458657HCID 49458657, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-bromobenzene-1-sulfonyl chloride (0.500 g, 1.96 mmol), 4-acetamidopiperidine (0.335 g, 2.45 mmol), and diisopropylethyl amine (1.0 mL, 5.8 mmol) in CH2Cl2 (5 mL) was stirred for 15 min at rt. The reaction mixture was then washed with 1 N HCl (2×5 mL) followed by brine (10 mL). The organic layer was isolated, dried over MgSO4, filtered, and concentrated to dryness to give the title compound (0.672 g, 95%). The product was used without further purification. 1H NMR (400 MHz, CDCl3) δ 8.09-8.05 (m, 1H), 7.77-7.74 (m, 1H), 7.49-7.38 (m, 2H), 6.08 (d, J=8.0, 1H), 3.87-3.79 (m, 2H), 2.93-2.85 (m, 2H), 2.00-1.93 (m, 5H), 1.59-1.51 (m, 3H).

Workup

  1. washThe reaction mixture was then washed with 1 N HCl (2×5 mL)
  2. customThe organic layer was isolated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-32bbf105ef95432f9663e33e95cf8091
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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