HCID 21467112, compound → HCID 70197290, compound

HRID 1939175Notes

Reaction equation

HRID 1939175 reaction equation
[O:1]=[C:2]1[CH:8]([NH:9][C:10](=[O:19])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:7]=[C:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]2[CH:26]=[CH:27][CH:28]=[CH:29][C:4]=2[N:3]1[CH3:30].[H][H]>CO.[Pd]>[O:1]=[C:2]1[C@@H:8]([NH:9][C:10](=[O:19])[CH2:11][CH2:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:7][C@@H:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]2[CH:26]=[CH:27][CH:28]=[CH:29][C:4]=2[N:3]1[CH3:30]

Participants

5

Reactant 2

HCID 21467112HCID 21467112, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70197290HCID 70197290, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of N-(2,3-Dihydro-2-oxo-1-methyl-5-phenyl-1H-1-benzazepin-3-yl)-3-cyclohexyl-propanamide (250 mg) in methanol (20 ml) was added to a suspension of 10% palladium on carbon (100 mg) in methanol (20 ml). This mixture was subjected to 50 psi of hydrogen on a Parr shaker for two hours. The mixture was then filtered over celite and concentrated at reduced pressure. The resulting foam was crystallized from a mixture of ethyl acetate and hexane, yielding a white solid (200 mg, 80%), which is a cis, racemic mixture. m.p. 156°-158° C.

Workup

  1. filtrationThe mixture was then filtered over celite
  2. concentrationconcentrated at reduced pressure
  3. customThe resulting foam was crystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-421f1bfdd8974d3094008568559a371b
Source dataset
uspto-grants-1997_12
Patent number
US05696111

Reaction notes

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