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 2059973Notes

Reaction equation

HRID 2059973 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)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 21.6 g (59.2 mmol) 3-(1-benzylpiperidin-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 DIPE, suction filtered, washed with DIPE and dried.

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 DIPE, suction
  5. filtrationfiltered
  6. washwashed with DIPE
  7. customdried

Sources & evidence

ORD record
ord-bc469d8f37a8425487d744df9001578c
Source dataset
uspto-grants-2012_10
Patent number
US08278336B2

Reaction notes

Loading…