2-Chloronicotinamide → 2-[4-(2,3-Dihydroxypropyl)piperazin-1-yl]nicotinamide

HRID 231764Notes

Reaction equation

HRID 231764 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[OH:11][CH:12]([CH2:20][OH:21])[CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C(O)C>[OH:11][CH:12]([CH2:20][OH:21])[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([NH2:6])=[O:5])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 825882-ChloronicotinamideHCID 1110023-(Piperazin-1-yl)propane-1,2-diol

Product 1

HCID 200320072-[4-(2,3-Dihydroxypropyl)piperazin-1-yl]nicotinamideYield 34.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Operation was carried out in a manner similar to the one described in Example 2, using 1.6 g of 2-chloronicotinamide, 3.2 g of 1-(2,3-dihydroxypropyl)piperazine and 30 ml ethanol and refluxing overnight. Column purification of the residue gave 1 g of 2-[4-(2,3-dihydroxypropyl)piperazin-1-yl]nicotinamide, which, recrystallized from acetone, melted at 140°-142° C.

Workup

  1. temperaturerefluxing overnight
  2. customColumn purification of the residue

Sources & evidence

ORD record
ord-0ef617aa10c541aea1bf538ef375577c
Source dataset
uspto-grants-1989_07
Patent number
US04849422

Reaction notes

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