Reaction #7238

Reaction equation

N-(1H-benzimidazol-2-ylmethyl)-N-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

5-n-butylpyridine-2-carboxaldehyde

NaBH(OAc)3

→

N-(5-butyl-2-pyridinylmethyl)-N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Solvents

CH2Cl2

Conditions

Workup

1. 1
   OtherPurification of the crude material by radial chromatography (2 mm TLC plate, 50:1:1 CH2Cl2: CH3OH: NH4OH)
2. 2
   Otherprovided 0.0713 g (45%) of AMD9398 (free base)

Procedure

Using general procedure B: N-(1H-benzimidazol-2-ylmethyl)-N-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.1258 g, 0.316 mmol) and 5-n-butylpyridine-2-carboxaldehyde (0.0603 g, 0.294 mmol) were reacted with NaBH(OAc)3 (0.0942 g, 0.444 mmol) in CH2Cl2 (2.5 mL). Purification of the crude material by radial chromatography (2 mm TLC plate, 50:1:1 CH2Cl2: CH3OH: NH4OH) provided 0.0713 g (45%) of AMD9398 (free base).

Source