Triethylamine → 1-(3-Nitropyridin-2-yl)-4-(3-phenylprop-2-ynyl)piperidin-4-ol

HRID 1896012Notes

Reaction equation

HRID 1896012 reaction equation
[C:1]1([C:7]#[C:8][CH2:9][C:10]2([OH:16])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=1.C(N(CC)CC)C>>[N+:24]([C:23]1[C:18]([N:13]2[CH2:14][CH2:15][C:10]([CH2:9][C:8]#[C:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([OH:16])[CH2:11][CH2:12]2)=[N:19][CH:20]=[CH:21][CH:22]=1)([O-:26])=[O:25]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 687253774-(3-Phenylprop-2-ynyl)piperidin-4-ol

Product 1

HCID 687266501-(3-Nitropyridin-2-yl)-4-(3-phenylprop-2-ynyl)piperidin-4-olYield 99.5%

Procedure

A well homogenised mixture of the Compound 256c (115 mg, 0.53 mmol), 2-chloro-3-nitropyridine (93.1 mg, 0.587 mmol) and triethyl amine (0.092 mL, 0.641 mmol) was stirred at 25° C. for 24 h. The reaction crude was purified by flash chromatography (EtOAc—Petroleum Ether 8:2) affording the title product (178 mg).

Workup

  1. stirringwas stirred at 25° C. for 24 h
  2. customThe reaction crude
  3. customwas purified by flash chromatography (EtOAc—Petroleum Ether 8:2)

Sources & evidence

ORD record
ord-baaa8fe2908040c69d5ca81c84d100d0
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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