Oxalyl chloride → 1-(Indole-5-carbonyl)-4-phenethylpiperazine

HRID 1586717

반응식

HRID 1586717 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(Cl)(=O)C(Cl)=O.[CH2:19]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C>C1COCC1.CN(C=O)C.ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([N:30]3[CH2:31][CH2:32][N:27]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:28][CH2:29]3)=[O:12])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

8

반응물 4

HCID 65578Oxalyl chlorideHCID 742801H-Indole-5-Carboxylic AcidHCID 792141-PhenethylpiperazineHCID 81531Diisopropylethylamine

생성물 1

HCID 149859971-(Indole-5-carbonyl)-4-phenethylpiperazine

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

Indole-5-carboxylic acid (57 mg, 0.35 mmol) was dissolved in THF(2 ml) and DMF (1 drop), then oxalyl chloride (37 μl, 54 mg, 0.42 mmol) was added. The mixture was stirred at room temperature for 3 hours, the solvent was evaporated under reduced pressure and the residue was dissolved in DMF (2 ml) and added to a stirred solution of 1-phenethylpiperazine (66 mg, 0.35 mmol) and diisopropylethylamine (91 μl, 68 mg, 0.52 mmol) in dichloromethane (1 ml). The mixture was stirred at room temperature for 24 hours, then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2 /CH3OH/NH3 ; 95:5:0.5 and crystallized from EtOAc/hexane to give the piperazine as microcrystals (32 mg, 27%), mp 105°-108° C.

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in DMF (2 ml)
  3. stirringThe mixture was stirred at room temperature for 24 hours
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with CH2Cl2 /CH3OH/NH3
  7. custom95:5:0.5 and crystallized from EtOAc/hexane

출처 및 근거

ORD 기록
ord-9ad5892176fa4175868669fa7ec7bcf5
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05215989

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