HCID 70565610, compound → HCID 70564912, compound

HRID 126918Notes

Reaction equation

HRID 126918 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]([C@H:10]2[C@H:14]([OH:15])[CH2:13][N:12]([CH2:16][CH3:17])[CH2:11]2)[CH3:9])=[O:7])=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[ClH:1].[CH2:16]([N:12]1[CH2:13][C@@H:14]([OH:15])[C@H:10]([N:8]([CH3:9])[C:6](=[O:7])[C:5]2[CH:18]=[CH:19][CH:2]=[CH:3][CH:4]=2)[CH2:11]1)[CH3:17]

Participants

5

Reactant 2

HCID 70565610HCID 70565610, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70564912HCID 70564912, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 14 g (49.5 mmoles) of trans-4-chloro-N-(1-ethyl-4-hydroxy-3-pyrrolidinyl)-N-methylbenzamide in 150 ml of absolute ethanol was treated with ca. 0.5 g of palladium-on-charcoal catalyst and was shaken with hydrogen at 60° C. in the Parr reduction apparatus for 3 hr. The mixture was cooled and filtered and the filtrate was concentrated. The residue crystallized when it was stirred with 3:1 diethyl ether-acetone. Separation of the precipitate gave 13.7 g (97%) of white powder; m.p. 160°-163° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated
  4. customThe residue crystallized when it
  5. customSeparation of the precipitate

Sources & evidence

ORD record
ord-3adafffc95464a53b942e03cae66e274
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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