Sodium Hydroxide → HCID 18964192, compound

HRID 2226997Notes

Reaction equation

HRID 2226997 reaction equation
Cl.[C:2]1([C:8]2([NH:14][C:15](=[O:17])[CH3:16])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].CS(O[CH2:25][CH2:26][CH:27]([C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([Cl:46])[CH:40]=1)[CH2:28][N:29]([CH3:38])[C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=O)=O>O>[ClH:45].[CH3:38][N:29]([CH2:28][CH:27]([C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([Cl:46])[CH:40]=1)[CH2:26][CH2:25][N:11]1[CH2:12][CH2:13][C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([NH:14][C:15](=[O:17])[CH3:16])[CH2:9][CH2:10]1)[C:30](=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18538563Acetamide, N-(4-phenyl-4-piperidinyl)-, monohydrochlorideHCID 18630858HCID 18630858, compound

Product 1

HCID 18964192HCID 18964192, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

22.7 g of 4-phenyl-4-acetylaminopiperidine hydrochloride are dissolved in 20 ml of water. 10 ml of concentrated sodium hydroxide solution are added. The mixture is extracted twice with dichloromethane and the organic phase is dried over MgSO4, The solution obtained is added to the product obtained in step 8. The mixture is concentrated to dryness, 30 ml of DMF are added and the mixture is heated to 70° C. for 1 h 30 min. The solution is poured very slowly onto 30 ml of water+ice. The precipitate is filtered off, taken up several times in water and drained. It is purified by chromatography on silica; elution: pure dichloromethane, then dichloromethane with addition of methanol up to 10%.

Workup

  1. extractionThe mixture is extracted twice with dichloromethane
  2. dry with materialthe organic phase is dried over MgSO4
  3. customThe solution obtained
  4. concentrationThe mixture is concentrated to dryness, 30 ml of DMF
  5. additionare added
  6. additionThe solution is poured very slowly onto 30 ml of water+ice
  7. filtrationThe precipitate is filtered off
  8. customIt is purified by chromatography on silica
  9. washelution
  10. additionpure dichloromethane, then dichloromethane with addition of methanol up to 10%

Sources & evidence

ORD record
ord-3da2de205c6346539508781b46f3b9bf
Source dataset
uspto-grants-1994_09
Patent number
US05350852

Reaction notes

Loading…