4-Phenylpiperidin-4-ol → HCID 70553233, compound

HRID 1447141Notes

Reaction equation

HRID 1447141 reaction equation
[C:1]([C:6]1[NH:7][C:8]([CH3:18])=[C:9]([CH3:17])[C:10]=1[O:11][CH2:12][CH:13]([OH:16])[CH2:14][Cl:15])([O:3][CH2:4][CH3:5])=[O:2].[OH:19][C:20]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>O1CCOCC1>[ClH:15].[CH2:4]([O:3][C:1]([C:6]1[NH:7][C:8]([CH3:18])=[C:9]([CH3:17])[C:10]=1[O:11][CH2:12][CH:13]([OH:16])[CH2:14][N:23]1[CH2:22][CH2:21][C:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([OH:19])[CH2:25][CH2:24]1)=[O:2])[CH3:5]

Participants

4

Reactant 2

HCID 963874-Phenylpiperidin-4-olHCID 20551463HCID 20551463, compound

Product 1

HCID 70553233HCID 70553233, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6.0 g of 1-(2-carboethoxy-4,5-dimethyl-pyrrol-3-oxy)-3-chloro-propan-2-ol and 3.5 g of 4-hydroxy-4-phenylpiperidine in 150 ml of dioxane are heated for 15 hours in an autoclave at 120° C. The volatile constituents are then distilled off under reduced pressure, and the very viscous crude product is partitioned between ether and 2 N sulfuric acid. The aqueous phase is cautiously rendered alkaline with 4 N sodium hydroxide solution and is then extracted with ether. The ether phase is dried over magnesium sulfate, the solvent is removed and the residue which remains is, as described in Example 2, dissolved in a small amount of methanol and treated with a solution of hydrogen chloride in ether, to give 3.2 g of 3-[2-hydroxy-3-(4-phenyl-4-hydroxy-piperidino)-propoxy]-4,5-dimethylpyrrole-2-carboxylic acid ethyl ester hydrochloride, of melting point 210°-212° C.

Workup

  1. distillationThe volatile constituents are then distilled off under reduced pressure
  2. customthe very viscous crude product is partitioned between ether and 2 N sulfuric acid
  3. extractionis then extracted with ether
  4. dry with materialThe ether phase is dried over magnesium sulfate
  5. customthe solvent is removed
  6. dissolutiondissolved in a small amount of methanol
  7. additiontreated with a solution of hydrogen chloride in ether

Sources & evidence

ORD record
ord-12b5d12c72d64c2b8ccf4ba6266c2c55
Source dataset
uspto-grants-1982_02
Patent number
US04315939

Reaction notes

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