Fumarate → HCID 86737533, compound

HRID 126922Notes

Reaction equation

HRID 126922 reaction equation
Cl[C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]([C@H:15]2[C@H:19]([OH:20])[CH2:18][N:17]([CH2:21][CH3:22])[CH2:16]2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[C:25]([O-:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([O-:30])=[O:29]>C(O)C.[Pd]>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[CH2:21]([N:17]1[CH2:18][C@@H:19]([OH:20])[C@H:15]([N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[O:7])[C:5]2[CH:23]=[CH:24][CH:2]=[CH:3][CH:4]=2)[CH2:16]1)[CH3:22]

Participants

5

Reactant 2

HCID 5460307FumarateHCID 70564945HCID 70564945, compound

Product 1

HCID 86737533HCID 86737533, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 6.4 g (0.0186 mole) of trans-4-chloro-N-(1-ethyl-4-hyroxy-3-pyrrolidinyl)-N-phenylbenzamide base in 75 ml of ethanol was hydrogenated over 10% palladium-on-charcoal at 60° overnight. The mixture was filtered through Celite and the filtrate was concentrated. The residue was partitioned between 10% sodium hydroxide and methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate and concentrated to give 5.6 g. (97%) of oil as residue. The oil was converted to the fumarate and the salt was recrystallized from 95% ethanol to yield an off-white powder; m.p. 191°-193° C.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was partitioned between 10% sodium hydroxide and methylene chloride
  4. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give 5.6 g
  7. customthe salt was recrystallized from 95% ethanol
  8. customto yield an off-white powder

Sources & evidence

ORD record
ord-993f3804d5fd431a945fcfae8ee8b3cf
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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