1-Benzyl-4-[N-methyl-N-(3-(formyl)-2-pyridinyl)amino]piperidine → HCID 53895921, compound

HRID 361793Notes

Reaction equation

HRID 361793 reaction equation
[CH2:1]([Li])[CH2:2]CC.[CH2:6]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]([CH3:28])[C:20]2[C:25]([CH:26]=O)=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1>[CH2:6]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]([CH3:28])[C:20]2[C:25]([CH:26]=[CH:1][CH3:2])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 108287021-Benzyl-4-[N-methyl-N-(3-(formyl)-2-pyridinyl)amino]piperidineHCID 178418339Butyllithium

Product 1

HCID 53895921HCID 53895921, compound

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring suspension of (ethyl)triphenylphosphonium bromide (1.75 g, 4.72 mmol) in dry THF (150 ml) at 20°-25° under nitrogen is added n-butyl lithium (1.6M in hexane, 2.95 ml, 4.72 mmol). The resulting mixture is stirred for 10 min followed by addition of 1-benzyl-4-[N-methyl-N-(3-formyl-2-pyridinyl)amino]piperidine (XXI, EXAMPLE 13, 1.40 g, 4.72 mmol) in THF (10 ml) under nitrogen. The mixture is stirred at 20°-25° for 1 hr and quenched with saturated aqueous ammonium chloride (50 ml). Water is added (100 ml) and the aqueous is extracted with ethyl acetate (3×75 ml). The organic phases are combined, dried over sodium sulfate and the solvent evaporated to dryness. The residue is purified via flash column chromatography (silica gel; hexane/ethyl acetate (6/1→1/1)) to give the title compound, NMR (CDCl3) 1.64, 1.81-1.93, 2.80, 2.91, 3.46, 5.77, 6.13, 6.26, 6.40, 6.78, 7.20-7.56 and 8.11δ; MS (EI, m/e) 321 (M+).

Workup

  1. stirringThe mixture is stirred at 20°-25° for 1 hr
  2. customquenched with saturated aqueous ammonium chloride (50 ml)
  3. additionWater is added (100 ml)
  4. extractionthe aqueous is extracted with ethyl acetate (3×75 ml)
  5. dry with materialdried over sodium sulfate
  6. customthe solvent evaporated to dryness
  7. customThe residue is purified via flash column chromatography (silica gel; hexane/ethyl acetate (6/1→1/1))

Sources & evidence

ORD record
ord-e924c7fdc67c45c49981edff31916719
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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