4-Nitrobenzaldehyde → HCID 11705489, compound

HRID 2167075Notes

Reaction equation

HRID 2167075 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][NH2:14])[CH2:7][CH2:6]1.[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)([O-:17])=[O:16].[BH4-].[Na+].[OH2:28]>C(O)C>[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:14][CH2:13][CH2:12][CH2:11][N:8]2[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][CH2:2][NH:1][CH2:22][C:21]3[CH:24]=[CH:25][C:18]([N+:15]([O-:16])=[O:28])=[CH:19][CH:20]=3)[CH2:10][CH2:9]2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 962WaterHCID 816291,4-Bis(3-aminopropyl)piperazineHCID 4311764Sodium borohydride

Product 1

HCID 11705489HCID 11705489, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 1,4-bis(3-aminopropyl)piperazine (0.513 mL, 2.49 mmol) and 4-nitrobenzaldehyde (792 mg, 5.24 mmol) in absolute ethanol (20 mL) was added 3 Å molecular sieves (5 g). After stirring the mixture for 12 h at room temperature, sodium borohydride (1.9 g, 49.9 mmol) was added and the mixture was stirred for 12 h under reflux. Then the reaction mixture was quentched by dropwise addition of water (20 mL) and ethanol was removed under reduced pressure. The aqueous residue was extracted with CH2Cl2 (3×30 mL) and the combined organic layers were extracted with HCl 1N (2×50 mL). The combined aqueous layers were neutralized with NaOH 1N (50 mL) and extracted with CH2Cl2 (3×30 mL). The combined organic layers were dried over MgSO4, evaporated to dryness and the oily residue purified by flash chromatography (neutral aluminium oxide, CH2Cl2/MeOH: 90/10).

Workup

  1. stirringthe mixture was stirred for 12 h
  2. temperatureunder reflux
  3. customwas removed under reduced pressure
  4. extractionThe aqueous residue was extracted with CH2Cl2 (3×30 mL)
  5. extractionthe combined organic layers were extracted with HCl 1N (2×50 mL)
  6. extractionextracted with CH2Cl2 (3×30 mL)
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. customevaporated to dryness
  9. customthe oily residue purified by flash chromatography (neutral aluminium oxide, CH2Cl2/MeOH: 90/10)

Sources & evidence

ORD record
ord-c4bec7fbe02f4283bf5f0d772885545f
Source dataset
uspto-grants-2015_06
Patent number
US09044478B2

Reaction notes

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