Potassium Iodide → 4-[4-(3-Piperidin-1-yl-propoxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1434569Notes

Reaction equation

HRID 1434569 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23]Cl)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 588178434-[4-(3-Chloro-propoxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 588178414-[4-(3-Piperidin-1-yl-propoxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-[4-(3-chloro-propoxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (D9) (4.0 g; 11.3 mM), piperidine (2.23 ml; 2 eq), potassium carbonate (3.73 g; 2.4 eq) and potassium iodide (3.74 g; 2 eq) in butan-2-one (100 ml) was heated at reflux for 3 days. The mixture was allowed to cool to room temperature, filtered and evaporated to give the title compound as a pale yellow solid (4.6 g)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 days
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f0d35fbe87d945dfbb15a4d5ae925b7c
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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