Triethylamine → HCID 17798577, compound

HRID 1840607Notes

Reaction equation

HRID 1840607 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][N:14]3[CH2:19][CH2:18][NH:17][CH2:16][C:15]3=[O:20])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[Br:28][C:29]1[CH:30]=[C:31]([S:35](Cl)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1>ClCCl>[Br:28][C:29]1[CH:30]=[C:31]([S:35]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH:10]3[CH2:11][CH2:12][N:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[CH2:8][CH2:9]3)[C:15](=[O:20])[CH2:16]2)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17943m-Bromobenzenesulphonyl chlorideHCID 10858694HCID 10858694, compound

Product 1

HCID 17798577HCID 17798577, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-[1-(4-pyridyl)-4-piperidylmethyl]-2-piperazinone (2.74 g) and triethylamine (1.67 ml) in dichioromethane (50 ml) was added dropwise at 0° C. 3-bromobenzenesulfonyl chloride (2.56 g), and the mixture was stirred at 0° C. for 1 hour. The reaction solution was diluted with dichioromethane, was washed with water and saturated brine, dried (MgSO4) and concentrated, and the residue was purified with silica gel column chromatography (acetone methanol=9:1=>1:1) and washed with water to give colorless crystals of 4-(3-bromobenzenesulfonyl)-1-[1-(4-pyridyl)-4-piperidylmethyl]-2-piperazinone (1.28 g). A part of the crystals were treated with hydrochloric acid to give colorless crystals of the title compound as hydrochloride.

Workup

  1. washwas washed with water and saturated brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customthe residue was purified with silica gel column chromatography (acetone methanol=9:1=>1:1)
  5. washwashed with water

Sources & evidence

ORD record
ord-f8d7618cf9674fd49c994ed566fc6237
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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