Piperazine → 1-(2-Methoxy-5-methylphenyl)piperazine

HRID 229354ノート

反応式

HRID 229354 の反応式
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:54]1[CH:59]=[C:58]([CH3:60])[CH:57]=[CH:56][C:55]=1[O:61][CH3:62].[NH:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1>C1(C)C=CC=CC=1>[CH3:62][O:61][C:55]1[CH:56]=[CH:57][C:58]([CH3:60])=[CH:59][C:54]=1[N:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1

参加物

6

反応物 4

HCID 4837PiperazineHCID 10796Cesium carbonateHCID 891432-Bromo-4-methylanisoleHCID 634876Binap, (A+-)-

生成物 1

HCID 193571151-(2-Methoxy-5-methylphenyl)piperazine収率 67.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

15 mg (0.016 mmol, 0.027 eq) Tris(dibenzylidene-acetone)dipalladium (0) (Pd2dba3), 27 mg (0.043 mmol, 0.072 eq) racemic-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl [(±)-BINAP] and 450 mg (1.38 mmol, 2.3 eq) cesium carbonate were combined in a microwave vial. 1.5 mL anhydrous toluene was added, followed by 121 mg (0.60 mmol, 1.0 eq) 2-bromo-4-methylanisole and 207 mg (2.40 mmol, 4.0 eq) piperazine. The vial was flushed with nitrogen prior to being microwaved at 140° C. for 30 minutes. The reaction mixture was diluted with 3.0 mL DMSO:methanol (1:1), filtered and purified by reverse-phase HPLC (2-99% CH3CN in 0.085% TFA (aq), 50 mL/min, 3×1.5 mL injected). Yield=83 mg (43%) of 1-(2-Methoxy-5-methyl-phenyl)-piperazine as a pale yellow oil (isolated as the mono-TFA salt);

後処理

  1. customThe vial was flushed with nitrogen
  2. customto being microwaved at 140° C. for 30 minutes
  3. additionThe reaction mixture was diluted with 3.0 mL DMSO:methanol (1:1)
  4. filtrationfiltered
  5. custompurified by reverse-phase HPLC (2-99% CH3CN in 0.085% TFA (aq), 50 mL/min, 3×1.5 mL injected)

出典と根拠

ORDレコード
ord-08d8e89934894921bc0a6c398c241777
出典データセット
uspto-grants-2009_07
特許番号
US07563795B2

反応ノート

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