Triethylamine → N-{2-[4-(3,4-dichlorophenoxy)-1-piperidinyl]ethyl}-3-(methylsulfonyl)benzamide hydrochloride

HRID 968760ノート

反応式

HRID 968760 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][NH2:14])[CH2:8][CH2:7]1.[CH3:19][S:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](O)=[O:27])(=[O:22])=[O:21].C(N(CC)CC)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][NH:14][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([S:20]([CH3:19])(=[O:22])=[O:21])[CH:24]=2)[CH2:10][CH2:11]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2203803-Methanesulfonylbenzoic acidHCID 2733179PyBroPHCID 113582094-(3,4-Dichlorophenoxy)-1-piperidineethanamine

生成物 1

HCID 69522044N-{2-[4-(3,4-dichlorophenoxy)-1-piperidinyl]ethyl}-3-(methylsulfonyl)benzamide hydrochloride収率 47.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The product of Step b (0.200 g) was dissolved in DMF (5 ml). 3-Methylsulphonyl-benzoic acid (0.132 g), triethylamine (0.250 ml) and PyBrop® (0.420 g) were added. After 24 hours at room temperature the solvents were evaporated and the residue redissolved in ethyl acetate. The organics were washed with H2O, dried with MgSO4 and concentrated. Purification by reverse phase HPLC (with a gradient eluent system (25% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%)) (any excess NH4OAc was removed by dissolving the compound in ethyl acetate and washing with aqueous saturated NaHCO3 followed by drying of the organics with MgSO4 and evaporation of solvent) and formation of the hydrochloride salt by addition of HCl dissolved in ether and evaporation of solvent gave the title compound (0.084 g).

後処理

  1. customAfter 24 hours at room temperature the solvents were evaporated
  2. dissolutionthe residue redissolved in ethyl acetate
  3. washThe organics were washed with H2O
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customPurification by reverse phase HPLC (with a gradient eluent system (25% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%)) (any excess NH4OAc
  7. customwas removed
  8. dissolutionby dissolving the compound in ethyl acetate
  9. washwashing with aqueous saturated NaHCO3
  10. customby drying of the
  11. customorganics with MgSO4 and evaporation of solvent) and formation of the hydrochloride salt
  12. additionby addition of HCl
  13. dissolutiondissolved in ether
  14. customevaporation of solvent

出典と根拠

ORDレコード
ord-923b376c0be44856a46b36ddc389e230
出典データセット
uspto-grants-2007_12
特許番号
US07304077B2

反応ノート

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