HCID 19874321, compound → HCID 67830907, compound

HRID 465370Notes

Reaction equation

HRID 465370 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]C)=[O:23])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1>CO.[OH-].[Na+]>[ClH:1].[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[O:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH2:15][CH2:16]2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 19874321HCID 19874321, compound

Product 1

HCID 67830907HCID 67830907, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 8.29 g of (±)-methyl 4-[(4-methylphenyl)-phenylmethoxy]-1-piperidinecaproate hydrochloride in 40 ml of methanol and 28 ml of 2N sodium hydroxide aqueous solution was refluxed for 1 hour and concentrated. Water was added to the residue, made acidic with hydrochloric acid and extracted with chloroform. The extract was dried and concentrated. The residue was solidified by treatment with ethyl acetate and ether. The precipitate was collected by filtration to give 7.73 g of colorless crystals. The crystals were then recrystallized from a mixture of water and acetone to give 5.80 g of colorless prisms, mp 168°~170° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationconcentrated
  3. additionWater was added to the residue
  4. extractionextracted with chloroform
  5. customThe extract was dried
  6. concentrationconcentrated
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-0257c391a4fa4a12b1f28337658083fb
Source dataset
uspto-grants-1992_10
Patent number
US05153207

Reaction notes

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