Hydrogen Bromide → HCID 70594250, compound

HRID 2049877Notes

Reaction equation

HRID 2049877 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:18][C:19]2[CH:24]=CC=CC=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:25](O)(=O)[C:26](O)=O.C(OC(C1(C2C=CC=CC=2SC2C=CC=CC=2)CCNCC1)=O)C.[Br:55][CH2:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1.C(=O)(O)[O-].[Na+].[I-].[K+].Br>CN(C)C=O.CCOCC>[BrH:55].[CH2:1]([O:3][C:4]([C:6]1([C:12]2[CH:24]=[CH:19][S:18][C:13]=2[C:14]2[CH:15]=[CH:16][CH:17]=[CH:26][CH:25]=2)[CH2:7][CH2:8][N:9]([CH:57]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[CH3:56])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

9

Reactant 6

HCID 260Hydrogen BromideHCID 4875Potassium IodideHCID 7666Phenethyl bromideHCID 516892Sodium BicarbonateHCID 20343975HCID 20343975, compoundHCID 20343976HCID 20343976, compound

Product 1

HCID 70594250HCID 70594250, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.67 g of 4-ethoxycarbonyl-4-(2-phenylthiophenyl)piperidine, free base of Example 17, 0.48 g of 2-bromoethylbenzene, 0.65 g of sodium bicarbonate and 0.65 g of potassium iodide in 15 ml of dimethylformamide is stirred at 60°-70° C. for 16 hours. Thereafter, the mixture is diluted with ether and the diluted mixture is filtered. The filtrate is concentrated in vacuo. The residue is purified by column chromatography (alumina column, ether eluant) to provide a purified product which, in ether, is converted to its hydrobromic acid salt. The salt is recrystallized from an acetone-ether mixture to provide 4-ethoxycarbonyl-1-phenylethyl-4-(2-phenylthiophenyl)piperidine hydrobromide.

Workup

  1. filtrationthe diluted mixture is filtered
  2. concentrationThe filtrate is concentrated in vacuo
  3. customThe residue is purified by column chromatography (alumina column, ether eluant)
  4. customto provide a purified product which
  5. customThe salt is recrystallized from an acetone-ether mixture

Sources & evidence

ORD record
ord-15c26c9bfc9f4dac9f4a141312410256
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

Loading…