Sodium borohydride → Paliperidone

HRID 448542Notes

Reaction equation

HRID 448542 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[CH2:24][CH2:25][CH2:26][C:27](=[O: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.[BH4-].[Na+]>CO.ClCCl>[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 4311764Sodium borohydrideHCID 446083593-{2-[4-(6-Fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-2-methyl-7,8-dihydro-4H-pyrido[1,2-a]pyrimidine-4,9(6H)-dione

Product 1

HCID 115237Paliperidone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl]ethyl]-9-oxo-2-methyl-6,7,8,9-tetrahydro-4H-pyrido-[1,2-a]pyrimidin-4-one (formula-10) (0.3 grams) taken in a mixture of methanol (1.5 ml) and dichloromethane (3 ml) added sodium borohydride (0.008 grams) and stirred for 1 hour at 30° C. The solvent was distilled off under reduced pressure. Methanol (1.5 ml) was added to it and heated to reflux for 30 min. the reaction mixture was cooled to 20° C. and stirred for 1 hour. Filtered the solid, washed with methanol and dried.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionMethanol (1.5 ml) was added to it
  3. temperatureheated
  4. temperatureto reflux for 30 min. the reaction mixture
  5. temperaturewas cooled to 20° C.
  6. stirringstirred for 1 hour
  7. filtrationFiltered the solid
  8. washwashed with methanol
  9. customdried

Sources & evidence

ORD record
ord-31fcfda66c1e45ac94a75421d21bf066
Source dataset
uspto-grants-2013_07
Patent number
US08481729B2

Reaction notes

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