Dimethylformamide → 1-(4-Indolyloxy)-3-[4-(2-naphthyl)piperazin-1-yl]propane oxalate

HRID 977356Notes

Reaction equation

HRID 977356 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH2:12][CH2:13]Cl)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.[C:31](=[O:34])([O-:33])[O-].[Na+].[Na+].CN(C)C=[O:40]>>[C:11]([OH:10])(=[O:40])[C:31]([OH:33])=[O:34].[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH2:12][CH2:13][N:28]3[CH2:27][CH2:26][N:25]([C:16]4[CH:17]=[CH:18][C:19]5[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=5)[CH:15]=4)[CH2:30][CH2:29]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 27601721-(Naphthalen-2-yl)piperazineHCID 116941694-(3-chloropropoxy)-1H-indole

Product 1

HCID 212683161-(4-Indolyloxy)-3-[4-(2-naphthyl)piperazin-1-yl]propane oxalate

Conditions

Temperature
100 °C

Procedure

1-(4-indolyloxy)-3-chloropropane (0.159 g, 0.75 mmol), 1-(2-naphthyl)piperazine (0.161 g, 0.75 mmol) and sodium carbonate (0.201 g, 1.89 mmol) were mixed together in 7 mL dimethylformamide and heated at 100° C. for 18 h. Evaporation of dimethylformamide, dilution with water and extractions with ethyl acetate provided 0.303 g. of oil. Crystallization as the oxalate salt from methanol provided 0.083 g of colorless crystals. Mp 209° C. Mass spectrum, m+ =385. Anal (C27H29N3O5) theory C, 68.20; H, 6.15; N, 8.84; found C, 68.47; H, 6.33; N, 8.60.

Workup

  1. customEvaporation of dimethylformamide, dilution
  2. extractionwith water and extractions with ethyl acetate
  3. customprovided 0.303 g
  4. customCrystallization as the oxalate salt from methanol

Sources & evidence

ORD record
ord-c3ac154afa0847be9b4a70b829ab3c23
Source dataset
uspto-grants-1997_03
Patent number
US05614523

Reaction notes

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