Piperonylamine → HCID 11292860, compound

HRID 1984566Notes

Reaction equation

HRID 1984566 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][CH2:11][C:12]2[S:16][C:15]([S:17](Cl)(=[O:19])=[O:18])=[CH:14][CH:13]=2)=[O:9])=[CH:4][CH:3]=1.O.Cl.[NH:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1>C(Cl)(Cl)Cl.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][CH2:11][C:12]2[S:16][C:15]([S:17]([N:23]3[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]3)(=[O:19])=[O:18])=[CH:14][CH:13]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2723901PiperonylamineHCID 27357135-((4-Chlorobenzamido)methyl)thiophene-2-sulfonyl chloride

Product 1

HCID 11292860HCID 11292860, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5-({[1-(4-Chloro-phenyl)-methanoyl]-amino}-methyl)-thiophene-2-sulfonyl chloride (1b) (5.0 g, 14 mmol) in 100 ml chloroform and a solution of 4-piperidinone hydrochloride monohydrate (4.3 g, 28 mmol) in 21 ml of NaOH (2N) were stirred vigorously for 15 h. The reaction was quenched with HCl (2N) and the organic layer was extracted twice with HCl (2N) and twice with brine. The dried organic phase affords after evaporation of chloroform 5.8 g (99.5%) of (63c) as a colourless solid: 1H NMR (CDCl3) δ7.67 (d, J=8.7 Hz, 2H), 7.42-7.38 (m, 3H), 6.99 (d, J=3.8 Hz, 1H), 6.53 (t, J=5.3 Hz, 1H), 4.74 (d, J=6.0 Hz, 2H), 3.37 (d, J=6.2 Hz, 4H), 2.50 (d, H=6.2 Hz, 4H).

Workup

  1. customThe reaction was quenched with HCl (2N)
  2. extractionthe organic layer was extracted twice with HCl (2N) and twice with brine
  3. customThe dried organic phase affords
  4. customafter evaporation of chloroform 5.8 g (99.5%) of (63c) as a colourless solid

Sources & evidence

ORD record
ord-120b831f2deb4d90add14a04c759b703
Source dataset
uspto-grants-2009_06
Patent number
US07544700B2

Reaction notes

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