3-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-9-hydroxy-2-methylpyrido[1,2-a]pyrimidin-4-one → Paliperidone

HRID 448545Notes

Reaction equation

HRID 448545 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]4[C:22](=[O:23])[N:21]5[CH:24]=[CH:25][CH:26]=[C:27]([OH:28])[C:20]5=[N:19][C:18]=4[CH3:29])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[H][H]>[C].[Pd].C(O)(=O)C>[CH3:29][C:18]1[N:19]=[C:20]2[N:21]([CH2:24][CH2:25][CH2:26][CH:27]2[OH:28])[C:22](=[O:23])[C:17]=1[CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH:9]([C:6]2[C:5]3[CH:30]=[CH:31][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 446025173-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-9-hydroxy-2-methylpyrido[1,2-a]pyrimidin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 115237Paliperidone

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl]ethyl]-9-hydroxy-2-methyl-4H-pyrido-[1,2-a]pyrimidin-4-one (formula-11) (5 grams), acetic acid (25 ml) and palladium carbon (4 grams) was taken in an autoclave. Hydrogen gas with a pressure of 3.0 Kg/cm2 was applied to the above mixture at 32° C. for 9 hrs. The reaction mixture was filtered through a hyflow bed. The filtrate was treated with water (100 ml) and the pH of the filtrate was adjusted to 10 using aqueous sodium hydroxide solution. The solid formed was filtered, washed with water and dried at 50° C. to yield the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through a hyflow bed
  2. additionThe filtrate was treated with water (100 ml)
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried at 50° C.

Sources & evidence

ORD record
ord-12dc37104a3a4eb2b446ecf9237aee85
Source dataset
uspto-grants-2013_07
Patent number
US08481729B2

Reaction notes

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