Benzaldehyde → 2-[3-(1-Benzylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine

HRID 1895959Notes

Reaction equation

HRID 1895959 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:3]=1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)Cl>O>[CH2:17]([N:14]1[CH2:13][CH2:12][C:11](=[CH:10][C:9]#[C:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=2)[CH2:16][CH2:15]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 875507132-[3-(1-Benzylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound of Example 3 (0.22 g, 1.04 mmol), benzaldehyde (0.13 mL, 1.25 mmol), sodium triacetoxyborohydride (0.33 g, 1.56 mmol) and 15 mL of CH2Cl2 was stirred overnight at r.t. Afterwards, it was diluted with water, the organic layer was separated, washed with brine (2×15 mL), dried (Na2SO4) and evaporated to dryness in vacuo the give a crude, which was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with a gradient Petroleum Ether-EtOAc from 85:15 to 0:100 affording the title compound, which was further purified by preparative RP LC-MS chromatography, using MS-C18 XTerra column 30×50 mm eluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient (0.12 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with brine (2×15 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness in vacuo the
  5. customgive a crude, which
  6. customwas purified by automated flash liquid chromatography (Horizon™-Biotage)
  7. washeluting with a gradient Petroleum Ether-EtOAc from 85:15 to 0:100 affording the title compound, which
  8. customwas further purified by preparative RP LC-MS chromatography
  9. washeluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient (0.12 g)

Sources & evidence

ORD record
ord-901dddb84a7b4df59e8fc54be1a54a92
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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