HCID 70051641, compound → HCID 70051928, compound

HRID 1885300Notes

Reaction equation

HRID 1885300 reaction equation
Cl.[NH2:2][C:3]1[C:31]([Cl:32])=[CH:30][C:6]([C:7]([NH:9][CH:10]2[CH2:14][CH:13]([CH2:15][OH:16])[N:12](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:11]2)=[O:8])=[C:5]([O:33][CH3:34])[CH:4]=1>CO.[Pd]>[ClH:32].[NH2:2][C:3]1[C:31]([Cl:32])=[CH:30][C:6]([C:7]([NH:9][CH:10]2[CH2:14][CH:13]([CH2:15][OH:16])[NH:12][CH2:11]2)=[O:8])=[C:5]([O:33][CH3:34])[CH:4]=1

Participants

4

Reactant 1

HCID 70051641HCID 70051641, compound

Product 1

HCID 70051928HCID 70051928, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a solution of 1.4 g of 4-amino-5-chloro-2-methoxy-N-(1-diphenylmethyl-5-hydroxymethyl pyrrolidin-3-yl) benzamide hydrochloride (Compound of Example 7) in methanol, 0.28 g of 5% palladium/carbon was added and hydrogenation was effected under normal pressure and temperature conditions. At the stage when 63 ml of hydrogen were consumed, the hydrogenation was discontinued and the reaction mixture was filtered to remove the catalyst and then concentrated under reduced pressure to precipitate crystals. The separated crystals were dispersed in aceton and filtered. Thus obtained crude product was recrystallized from ethanol to obtain 0.46 g of 4-amino-5-chloro-2-methoxy-N-(5-hydroxymethyl pyrrolidin 3-yl) benzamid hydrochloride

Workup

  1. customAt the stage when 63 ml of hydrogen were consumed
  2. filtrationthe reaction mixture was filtered
  3. customto remove the catalyst
  4. concentrationconcentrated under reduced pressure
  5. customto precipitate crystals
  6. additionThe separated crystals were dispersed in aceton
  7. filtrationfiltered
  8. customThus obtained crude product
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-c5a48736f6674247a7f4cea74396b3ba
Source dataset
uspto-grants-1992_09
Patent number
US05143935

Reaction notes

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