1,3,4,5-Tetrahydro-3-[1-(phenylmethyl)-4-piperidinyl]-2H-1,3-benzodiazepin-2-one → 3-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

HRID 2378933Notes

Reaction equation

HRID 2378933 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[NH:16][C:15]2=[O:25])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[NH:16][C:15]2=[O:25])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 162024881,3,4,5-Tetrahydro-3-[1-(phenylmethyl)-4-piperidinyl]-2H-1,3-benzodiazepin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(1-Benzylpiperidin-4-yl)-4,5-dihydro-1H-benzo [d][1,3]diazepin-2(3H)-one (1.30 g, 3.88 mmol) was dissolved in methanol (50 ml). 10% Palladium on carbon (650 mg) was added to the mixture. Reaction vessel was placed on a Parr apparatus and charged with 60 psi of hydrogen gas. Reaction shook at room temperature for 15 hours. Reaction was removed from the apparatus. Mixture was filtered through a 0.45 μm PVDF membrane. Filtrate was concentrated to dryness. Title compound was obtained as white solid in 82% yield. MS (M+H)+=246.4.

Workup

  1. customReaction vessel
  2. customReaction
  3. customReaction
  4. customwas removed from the apparatus
  5. filtrationMixture was filtered through a 0.45 μm PVDF membrane
  6. concentrationFiltrate was concentrated to dryness

Sources & evidence

ORD record
ord-e1e8e81c378a45b1bcb852edd4531506
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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