1-[5-(Benzyloxy)pyridin-2-yl]-4-(methanesulfonyl)piperazine → 6-[4-(Methanesulfonyl)piperazin-1-yl]pyridin-3-ol

HRID 1723812Notes

Reaction equation

HRID 1723812 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][CH2:16]2)=[N:13][CH:14]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[CH3:24][S:21]([N:18]1[CH2:17][CH2:16][N:15]([C:12]2[N:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[CH2:20][CH2:19]1)(=[O:23])=[O:22]

Participants

3

Reactant 1

HCID 688458821-[5-(Benzyloxy)pyridin-2-yl]-4-(methanesulfonyl)piperazine

Product 1

HCID 688451756-[4-(Methanesulfonyl)piperazin-1-yl]pyridin-3-olYield 97,122.297%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-[5-(benzyloxy)pyridin-2-yl]-4-(methylsulfonyl)piperazine (120 g, 278 mmol) was dissolved in TFA (1.3 L) and the reaction heated to reflux, with stirring, for 3 hours then cooled to room temperature. The TFA was then removed in vacuo and the residue azeotroped with toluene (2×300 mL). The resulting liquor was diluted with DCM (100 mL) and slowly neutralised to pH8 with sat. NaHCO3 (700 mL). The suspension was filtered, washed with water, minimum DCM and ether and dried to give 6-[4-(methylsulfonyl)piperazin-1-yl]pyridin-3-ol as a beige solid (69 g, 270 mol, 97%).

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux
  3. customThe TFA was then removed in vacuo
  4. customthe residue azeotroped with toluene (2×300 mL)
  5. additionThe resulting liquor was diluted with DCM (100 mL) and slowly neutralised to pH8 with sat. NaHCO3 (700 mL)
  6. filtrationThe suspension was filtered
  7. washwashed with water, minimum DCM and ether
  8. customdried

Sources & evidence

ORD record
ord-3bb5260308224790a5d5b031014b89b4
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

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