Water → HCID 11547528, compound

HRID 2167060Notes

Reaction equation

HRID 2167060 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]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH:25]=O)=[CH:17][CH:16]=1.[BH4-].[Na+].O>C(O)C>[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH2:25][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][CH2:25][C:18]3[C:19]4[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:15]=[CH:16][CH:17]=3)[CH2:10][CH2:9]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 780724-QuinolinecarboxaldehydeHCID 816291,4-Bis(3-aminopropyl)piperazineHCID 4311764Sodium borohydride

Product 1

HCID 11547528HCID 11547528, 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-quinolinecarboxaldehyde (824 mg, 5.24 mmol) in absolute ethanol (20 mL), 3 Å molecular sieves are added. After stirring the mixture at room temperature for 12 h, NaBH4 (1.9 g, 249.92 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 by flash chromatography on neutral aluminium oxide (CH2Cl2/MeOH).

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 by flash chromatography on neutral aluminium oxide (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-618a51fbb39f4217907580f0ab894709
Source dataset
uspto-grants-2015_06
Patent number
US09044478B2

Reaction notes

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