HCID 67655068, compound → HCID 54555986, compound

HRID 2393425Notes

Reaction equation

HRID 2393425 reaction equation
[N+:1]([CH:4]1[CH2:9][NH:8][CH2:7][CH2:6][N:5]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=O>C(O)C.O=[Pt]=O>[NH2:1][CH:4]1[CH2:9][NH:8][CH2:7][CH2:6][N:5]1[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 67655068HCID 67655068, compound

Product 1

HCID 54555986HCID 54555986, compoundYield 183.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

Reaction of Intermediate 2 with 4-nitrobenzaldehyde under standard reductive amination conditions gave 1-(3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl)-4-(4-(nitro)benzyl)piperazine in 46% yield. PtO2 (60 mg) was suspended in ethanol (40 ml) and stirred under an atmosphere of hydrogen for 0.75 h. The preceding nitrobenzyl piperazine (0.33 g, 0.74 mmol) was then added and the mixture stirred for 2 h. The catalyst was removed by filtration through celite, the solvent removed under vacuum and the residue chromatographed on silica gel eluting with CH2Cl2 /MeOH/NH3 (70:8:1) to give the title-amino-benzyl piperazine (0.26 g, 85%). The 4.1 hydrogen oxalate salt was prepared: mp 150°-153° C. (Found: C, 49.04; H, 4.80; N, 12.76. C24H29N7.4.1(C2H2O4) requires C, 49.28; H, 4.77; N, 12.49%); m/e 416 (M+1)+ ; δ (250 MHz, d6 -DMSO; free base) 1.72-1.86 (2H, m, CH2); 2.16-2.44 (10H, m, 5 of CH2); 2.70 (2H, t, J=7.4Hz, CH2); 3.23 (2H, s, CH2); 4.93 (2H, s, NH2); 6.48 (2H, d, J=8.4Hz, Ar-H); 6.89 (2H, d, J=8.4Hz, Ar-H); 7.27 (1H, s, Ar-H); 7.29 (1H, dd, J=2.1 and 8.6Hz, Ar-H); 7.47 (1H, d, J=8.6Hz, Ar-H); 7.78 (1H, d, J=2.1Hz, Ar-H); 9.02 (2H, s, Triazole-H); 11.07 (1H, s, NH).

Workup

  1. stirringthe mixture stirred for 2 h
  2. customThe catalyst was removed by filtration through celite
  3. customthe solvent removed under vacuum
  4. customthe residue chromatographed on silica gel eluting with CH2Cl2 /MeOH/NH3 (70:8:1)

Sources & evidence

ORD record
ord-ce948818533b419480fcd37ed0f3b694
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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