Hydrochloric Acid → 4-[2-(Piperazin-1-yl)ethoxy]-2,6-bis(hydroxymethyl)pyridine

HRID 446651Notes

Reaction equation

HRID 446651 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[C:22]([CH2:24][OH:25])[N:21]=[C:20]([CH2:26][OH:27])[CH:19]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>O1CCOCC1>[N:12]1([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[C:22]([CH2:24][OH:25])[N:21]=[C:20]([CH2:26][OH:27])[CH:19]=2)[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 670321474-(2-(4-(Tert-butoxycarbonyl)piperazin-1-yl)ethoxy)-2,6-bis(hydroxymethyl)pyridine

Product 1

HCID 670322814-[2-(Piperazin-1-yl)ethoxy]-2,6-bis(hydroxymethyl)pyridineYield 95.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

19 ml of a 4M solution of HCl in dioxane are added to 2.3 g of 4-(2-(4-(tert-butoxycarbonyl)piperazin-1-yl)ethoxy)-2,6-bis(hydroxymethyl)pyridine in solution in 33 ml of dioxane. After 12 h at AT, the resulting precipitate is recovered by filtration on a sintered glass funnel, taken up in MeOH and then concentrated under RP, and the residue is diluted in 40 ml of an MeOH/water 1/1 mixture. The resulting solution is deposited on Mega BE-SCX, 25GM 150ML (Varian). After washing the phase with MeOH, the product of interest is eluted with a 2N solution of ammonia in methanol. The MeOH/NH3 phase is concentrated under RP. 1.6 g of 4-[2-(piperazin-1-yl)ethoxy]-2,6-bis(hydroxymethyl)pyridine are thus obtained.

Workup

  1. filtrationthe resulting precipitate is recovered by filtration on a sintered glass funnel
  2. concentrationconcentrated under RP
  3. additionthe residue is diluted in 40 ml of an MeOH/water 1/1 mixture
  4. washAfter washing the phase with MeOH
  5. washthe product of interest is eluted with a 2N solution of ammonia in methanol
  6. concentrationThe MeOH/NH3 phase is concentrated under RP

Sources & evidence

ORD record
ord-35f06972dcad48eaabbfc7a028de31db
Source dataset
uspto-grants-2013_07
Patent number
US08481042B2

Reaction notes

Loading…