Sodium Carbonate → HCID 20513944, compound

HRID 1902834Notes

Reaction equation

HRID 1902834 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:17]([C:20]1[CH:30]=[CH:29][C:23]([O:24][CH2:25][CH2:26][CH2:27][Cl:28])=[C:22]([O:31][CH3:32])[CH:21]=1)(=[O:19])[CH3:18].C(=O)([O-])[O-].[Na+].[Na+]>C(OC(=O)C)C(C)C>[ClH:28].[C:17]([C:20]1[CH:30]=[CH:29][C:23]([O:24][CH2:25][CH2:26][CH2:27][N:11]2[CH2:12][CH2:13][C:8]([C:6](=[O:7])[C:5]3[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=3)([OH:14])[CH2:9][CH2:10]2)=[C:22]([O:31][CH3:32])[CH:21]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 15105361HCID 15105361, compound

Product 1

HCID 20513944HCID 20513944, compound

Reagents, catalysts & solvents 1

HCID 8038Isobutyl AcetateSolvent

Procedure

A stirred mixture of 11.1 g (0.05 mole) of 4-(p-fluorobenzoyl)-4-hydroxy-piperidine, 14.6 g (0.06 mole) of 3-(p-acetyl-o-methoxyphenoxy)-propyl chloride and 25 g of anhydrous sodium carbonate in 350 ml iso-butylacetate was allowed to reflux for 48 h. The mixture was filtered and the filtrate was concentrated under vacuum. The residual oil was converted to the HCl salt. 1-[3-(p-Acetyl-o-methoxyphenoxy)propyl]-4-(p-fluorobenzoyl)-4-hydroxy-piperidine hydrochloride was recrystallised from ethanol. Melting point 160°-162° C. Yield 16.2 g. Said product contained a certain amount of ethanol which can only be removed by extreme means.

Workup

  1. temperatureto reflux for 48 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. custom1-[3-(p-Acetyl-o-methoxyphenoxy)propyl]-4-(p-fluorobenzoyl)-4-hydroxy-piperidine hydrochloride was recrystallised from ethanol
  5. customcan only be removed by extreme means

Sources & evidence

ORD record
ord-450a526b2330431d98308c0a4af28960
Source dataset
uspto-grants-1982_12
Patent number
US04366162

Reaction notes

Loading…