Potassium Iodide → 1-[4,4-Bis(4-fluorophenyl)butyl]-4-ethoxycarbonylaminopiperidine

HRID 2073492Notes

Reaction equation

HRID 2073492 reaction equation
[CH2:1]([O:3][C:4]([NH:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:5])[CH3:2].[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:21][CH2:22][CH2:23]Br)=[CH:16][CH:15]=1.C(N(CC)CC)C.[I-].[K+]>CN(C)C=O.O.[OH-].[Na+]>[F:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[CH2:21][CH2:22][CH2:23][N:10]2[CH2:11][CH2:12][CH:7]([NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:8][CH2:9]2)=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 937631,1'-(4-Bromobutylidene)bis[4-fluorobenzene]HCID 15595030ethyl N-(piperidin-4-yl)carbamate

Product 1

HCID 138832851-[4,4-Bis(4-fluorophenyl)butyl]-4-ethoxycarbonylaminopiperidine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

11 g (64 mmol) of 4-ethoxycarbonylaminopiperidine, 20.5 g (64 mmol) of 4,4-bis(4-fluorophenyl)butyl bromide, 12.9 g (128 mmol) of triethylamine and 0.18 g of potassium iodide were stirred in 180 ml of absolute dimethylformamide at 80° C. for 36 hours, the mixture was diluted with about 1.5 liters of water, 100 ml of 2N NaOH were added and the mixture was extracted twice with methylene chloride.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted twice with methylene chloride

Sources & evidence

ORD record
ord-8c64d4447cf1421f885c9da78776b5a9
Source dataset
uspto-grants-1990_04
Patent number
US04918073

Reaction notes

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