Water → HCID 11711391, compound

HRID 2167063Notes

Reaction equation

HRID 2167063 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.[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.O>C(O)C>[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][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][CH2:20][C:19]3[CH:22]=[CH:23][C:16]([F:15])=[CH:17][CH:18]=3)[CH2:10][CH2:9]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 680234-FluorobenzaldehydeHCID 816291,4-Bis(3-aminopropyl)piperazine

Product 1

HCID 11711391HCID 11711391, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 1,4-bis(3-aminopropyl)piperazine (0.51 mL, 2.5 mmol) and 4-fluorobenzaldehyde (0.59 mL, 5.5 mmol) in absolute ethanol (20 mL), 3 Å molecular sieves are added. After stirring the mixture at room temperature for 5 h, NaBH (0.47 g, 12.5 mmol) was added portionwise and the mixture was stirred for 12 h at room temperature. The reaction 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). Combined organic layers were extracted with HCl 1M. The combined aqueous layers were neutralized with NaOH 1M and extracted with CH2Cl2. Combined organic layers were dried over MgSO4. Crude compound is purified thick-layer chromatography (acetone/NH4OH:90/10).

Workup

  1. stirringthe mixture was stirred for 12 h at room temperature
  2. customwas removed under reduced pressure
  3. extractionThe aqueous residue was extracted with CH2Cl2 (3×30 mL)
  4. extractionCombined organic layers were extracted with HCl 1M
  5. extractionextracted with CH2Cl2
  6. dry with materialCombined organic layers were dried over MgSO4
  7. customCrude compound is purified thick-layer chromatography (acetone/NH4OH:90/10)

Sources & evidence

ORD record
ord-25b8026614bb4f15a6f333d3d05f4ce8
Source dataset
uspto-grants-2015_06
Patent number
US09044478B2

Reaction notes

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