2-Chloronicotinic acid → 2-[4-(3-Hydroxypropyl)piperazin-1-yl]nicotinic acid

HRID 231770Notes

Reaction equation

HRID 231770 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.Cl[C:12]1[N:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]>O1CCOCC1>[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:12]2[N:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 762582-Chloronicotinic acidHCID 79207Piperazin-1-ylpropanol

Product 1

HCID 200319982-[4-(3-Hydroxypropyl)piperazin-1-yl]nicotinic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Grams 8.65 of 1-(3-hydroxypropyl)piperazine and 4.7 g of 2-chloronicotinic acid in 100 ml dioxane were refluxed for 6 hours. The reaction mixture was cooled and settled. The residual oil, crystallized from 95° ethanol, gave 2.3 g of 2-[4-(3-hydroxypropyl)piperazin-1-yl]nicotinic acid, melting at 222°-225° C. (with decomposition).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe residual oil, crystallized from 95° ethanol

Sources & evidence

ORD record
ord-516657a43b184a9dbceb122c90d21b94
Source dataset
uspto-grants-1989_07
Patent number
US04849422

Reaction notes

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