3-(1-Benzylpiperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one → 7-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

HRID 469292Notes

Reaction equation

HRID 469292 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:20][CH2:19][C:18]3[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:17]=3[NH:16][C:15]2=[O:27])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].CO>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:17]2[NH:16][C:15](=[O:27])[N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH2:20][CH2:19][C:18]=2[CH:21]=1

Participants

5

Reactant 2

HCID 596268033-(1-Benzylpiperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 183568527-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 21.6 g (59.2 mmol) 3-(1-benzyl-piperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 2.5 g palladium on charcoal (10%) in 300 mL methanol was hydrogenated in a 3 bar hydrogen atmosphere at 50° C. until the reaction was complete. The catalyst was removed by suction filtering and the mother liquor was concentrated by rotary evaporation. The residue was triturated with 150 mL DIPE, suction filtered, washed with 100 mL DIPE and dried at 40° C. in the CAD. 13.2 g of the desired product was obtained.

Workup

  1. customThe catalyst was removed by suction
  2. filtrationfiltering
  3. concentrationthe mother liquor was concentrated by rotary evaporation
  4. customThe residue was triturated with 150 mL DIPE, suction
  5. filtrationfiltered
  6. washwashed with 100 mL DIPE
  7. customdried at 40° C. in the CAD

Sources & evidence

ORD record
ord-b94b42e46b4441aa8d74a637019ff2aa
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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