Dimethylcarbamoyl Chloride → 4-[[(1-Piperidinyl)methylene]amino]-3-pyridinol N,N-dimethylcarbamate

HRID 399399

Reaction equation

HRID 399399 reaction equation
[N:1]1([CH:7]=[N:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[OH:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:23][N:24]([CH3:28])[C:25](Cl)=[O:26]>O1CCCC1>[CH3:23][N:24]([CH3:28])[C:25]([O:15][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[N:8]=[CH:7][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:26]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 153809334-[[(1-Piperidinyl)methylene]amino]-3-pyridinol

Product 1

HCID 677490704-[[(1-Piperidinyl)methylene]amino]-3-pyridinol N,N-dimethylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture prepared from 4-[[(1-piperidinyl)methylene]amino]-3-pyridinol (3.5 g), triethylamine (3.69 mL), dimethylcarbamyl chloride (2.3 mL) and tetrahydrofuran (130 mL) was refluxed for 2 hours, filtered, poured directly onto a silica column and eluted successively with ethyl acetate and 5% Et3N/ethyl acetate to yield 4.49 g of product. Recrystallization from ethyl acetate and drying under high vacuum yielded 3.94 g of crystals, m.p. 88°-89° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationfiltered
  3. additionpoured directly onto a silica column
  4. washeluted successively with ethyl acetate and 5% Et3N/ethyl acetate

Sources & evidence

ORD record
ord-bb27e87aae9148568f642653538c1581
Source dataset
uspto-grants-1998_10
Patent number
US05821239

Linked notes

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