HCID 54196075, compound → HCID 54458996, compound

HRID 1489195Notes

Reaction equation

HRID 1489195 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][C:26]([C:36]([O:38]C)=[O:37])([N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][C:30]3=[O:35])[CH2:25][CH2:24]2)[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]>O1CCCC1.[OH-].[Na+]>[C:36]([C:26]1([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][C:30]2=[O:35])[CH2:25][CH2:24][N:23]([CH2:22][CH2:21][C@@H:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:28][CH2:27]1)([OH:38])=[O:37]

Participants

4

Reactant 1

HCID 54196075HCID 54196075, compound

Product 1

HCID 54458996HCID 54458996, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of (S)-N-[2-(3,4-dichlorophenyl)-4-[4-methoxycarbonyl-4-(2-oxopiperidino)piperidino]butyl]-N-methylbenzamide (0.65 g) in tetrahydrofuran (15 mL) and 1.0N sodium hydroxide (15.5 mL) was heated at reflux overnight. After the tetrahydrofuran was distilled off, the resulting aqueous mixture was adjusted to a pH of 5.5-6.0 and extracted several times with dichloromethane. The organic extracts were dried and evaporated. The crude product was suspended in ether and filtered to give the title compound as a white solid (0.25 g); MS: m/z=560(M+1).

Workup

  1. temperatureat reflux overnight
  2. distillationAfter the tetrahydrofuran was distilled off
  3. extractionextracted several times with dichloromethane
  4. customThe organic extracts were dried
  5. customevaporated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-0c909a452136498ca5489afba344687a
Source dataset
uspto-grants-1997_10
Patent number
US05677317

Reaction notes

Loading…