Sodium Carbonate → HCID 70552636, compound

HRID 1447140Notes

Reaction equation

HRID 1447140 reaction equation
[C:1]([C:6]1[NH:7][C:8]([CH3:17])=[C:9]([CH3:16])[C:10]=1[O:11][CH2:12][CH2:13][CH2:14][Cl:15])([O:3][CH2:4][CH3:5])=[O:2].[OH:18][C:19]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[ClH:15].[CH2:4]([O:3][C:1]([C:6]1[NH:7][C:8]([CH3:17])=[C:9]([CH3:16])[C:10]=1[O:11][CH2:12][CH2:13][CH2:14][N:22]1[CH2:21][CH2:20][C:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([OH:18])[CH2:24][CH2:23]1)=[O:2])[CH3:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 963874-Phenylpiperidin-4-olHCID 12895167HCID 12895167, compound

Product 1

HCID 70552636HCID 70552636, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 g of 1-(2-carboethoxy-4,5-dimethyl-pyrrol-3-oxy)-3-chloropropane, 35 g of 4-hydroxy-4-phenyl-piperidine and 50 g of sodium carbonate in 300 ml of N,N-dimethylformamide are heated for 20 hours at 100° C. When the mixture has cooled, it is partitioned between water and methylene chloride, the organic phase is evaporated under reduced pressure, the residue which remains in dissolved in a small amount of methanol, and a solution of hydrogen chloride in ether is added dropwise. The crystals which precipitate are filtered off, washed with ether and dried. 56 g of 3-[3-(4-phenyl-4-hydroxy-piperidino)-propoxy]-4,5-dimethylpyrrole-2-carboxylic acid ethyl ester hydrochloride, of melting point 165°-169° C., are obtained.

Workup

  1. temperatureWhen the mixture has cooled
  2. customit is partitioned between water and methylene chloride
  3. customthe organic phase is evaporated under reduced pressure
  4. dissolutionin dissolved in a small amount of methanol
  5. additiona solution of hydrogen chloride in ether is added dropwise
  6. filtrationThe crystals which precipitate are filtered off
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-5e446582324240849d22b7f67bf22298
Source dataset
uspto-grants-1982_02
Patent number
US04315939

Reaction notes

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