Lithium diisopropylamide → HCID 22992262, compound

HRID 1350112Notes

Reaction equation

HRID 1350112 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH:6](N)[CH2:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:2]1.CS(OC1CCOCC1)(=O)=O.[Li+].CC([N-:30]C(C)C)C>>[O:1]1[CH2:2][CH2:3][CH:6]([CH:7]([NH2:30])[C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 11344352Oxan-4-yl methanesulfonateHCID 63562658HCID 63562658, compound2×

Product 1

HCID 22992262HCID 22992262, compoundYield 52%

Procedure

The 1-(4-oxanyl)-1-(3-pyridyl)methylamine was synthesized essentially according to the procedure described above for the synthesis of 1-(3-oxolanyl)-2-(3-pyridyl)ethylamine. Thus, 4-oxanyl methanesulfonate (0.99 g, 5.5 mmol), prepared according to the procedure of Suto et al., J. Med. Chem., 34: 2484 (1991), was treated with the imine anion generated by reacting N-(diphenylmethylidene)-3-(aminomethyl)pyridine (1.36 g, 5.0 mmol) with LDA (5.5 mmol in 5.0 mL THF). A work up similar to the one described for the synthesis of 1-(3-oxolanyl)-2-(3-pyridyl)ethylamine, followed by purification by column chromatography (15% methanol in chloroform), yielded 1-(4-oxanyl)-1-(3-pyridyl)methylamine (499 mg, 52% yield).

Workup

  1. customThe 1-(4-oxanyl)-1-(3-pyridyl)methylamine was synthesized essentially
  2. customfollowed by purification by column chromatography (15% methanol in chloroform)

Sources & evidence

ORD record
ord-0a6244de06f044b38b529449ff510f40
Source dataset
uspto-grants-2007_05
Patent number
US07214686B2

Reaction notes

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