Tetrahydrofuran → n-(2-Pyridinylmethyl)-n'-(1,2,3,4-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

HRID 351158Notes

Reaction equation

HRID 351158 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH2:9][CH2:8][CH2:7]2.[CH2:12]1[CH2:16]O[CH2:14][CH2:13]1.[BH3-][C:18]#[N:19].[Na+]>C1C=CC=CC=1>[N:10]1[CH:9]=[CH:8][CH:14]=[CH:13][C:12]=1[CH2:16][NH:19][CH2:18][C:3]1[CH:2]=[CH:11][C:6]([CH2:7][NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[NH:10][CH2:9][CH2:8][CH2:7]3)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 1046728-Quinolinamine, 1,2,3,4-tetrahydro-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 22256411n-(2-Pyridinylmethyl)-n'-(1,2,3,4-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of 8-amino-1,2,3,4-tetrahydroquinoline (0.136 g, 0.92 mmol) and N-[1-methylene-4-(carboxaldehyde)phenylene]-N-(2-nitrobenzenesulfonyl)-2-(aminomethyl)pyridine (0.370 g, 0.90 mmol) in benzene (20 mL) was heated to reflux under Dean-Stark conditions for 24 hours. The mixture was concentrated, dissolved in MeOH (10 mL) and THF (2 mL) and treated with NaBH3CN (0.094 g, 1.49 mmol) for 72 hours. The mixture was concentrated and partitioned between CH2Cl2 (20 mL) and a 1.0 M aqueous solution of NaOH (5 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by flash chromatography (24 g silica gel, 20:1 CH2Cl2-CH3OH) gave the desired product (0.137 g).

Workup

  1. temperatureto reflux under Dean-Stark conditions for 24 hours
  2. concentrationThe mixture was concentrated
  3. dissolutiondissolved in MeOH (10 mL)
  4. concentrationThe mixture was concentrated
  5. custompartitioned between CH2Cl2 (20 mL)
  6. customThe phases were separated
  7. extractionthe aqueous phase was extracted with CH2Cl2 (3×10 mL)
  8. dry with materialThe combined organic extracts were dried (Na2SO4)
  9. concentrationconcentrated
  10. customPurification of the crude material by flash chromatography (24 g silica gel, 20:1 CH2Cl2-CH3OH)

Sources & evidence

ORD record
ord-4c7a790444d5414b8591df601449cac3
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

Loading…