Sodium Hydroxide → HCID 53934672, compound

HRID 397752Notes

Reaction equation

HRID 397752 reaction equation
C([N:3]1[CH2:8][CH2:7][C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH:19]([CH3:21])[CH3:20])[CH:13]=2)([CH2:9][CH2:10][CH3:11])[CH2:5][CH2:4]1)C.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24].[OH-].[Na+]>C1(C)C=CC=CC=1>[NH3:3].[C:26]1([O:25][C:23]([N:3]2[CH2:4][CH2:5][C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH:19]([CH3:21])[CH3:20])[CH:13]=3)([CH2:9][CH2:10][CH3:11])[CH2:7][CH2:8]2)=[O:24])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 23001016HCID 23001016, compound

Product 2

HCID 222AmmoniaHCID 53934672HCID 53934672, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To N-ethyl-4-(3-(1-methylethoxy)phenyl)-4-n-propylpiperidine (Preparation 65, 10.9 g) in toluene (80 ml) under nitrogen at 85° C. was slowly added phenyl chloroformate (5.63 ml, 44.88 mmol) over 20 min. The mixture was then heated under reflux for 4 h. The solution was cooled to 50° C. and 5M aqueous sodium hydroxide (10 ml) was added. Once the solution had cooled to room temperature the layers were separated and the organic extract was washed with methanol:1N aqueous hydrochloric acid (1:1, 2×10 ml), methanol 1N aqueous sodium hydroxide solution (1:1, 20 ml) and water (20 ml). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give the crude product. This was purified by silica column chromatography using ethyl acetate:hexane:0.880 ammonia (15:85:1) to give the title compound as a pale yellow oil (6.9 g, 42% over three steps).

Workup

  1. customat 85° C.
  2. customover 20 min
  3. temperatureThe mixture was then heated
  4. temperatureunder reflux for 4 h
  5. temperatureOnce the solution had cooled to room temperature the layers
  6. customwere separated
  7. extractionthe organic extract
  8. washwas washed with methanol
  9. dry with materialThe organic layer was dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto give the crude product
  13. customThis was purified by silica column chromatography

Sources & evidence

ORD record
ord-38c5b7bdfee449f280e2a66c71c2c527
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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