Potassium Carbonate → 4-(2-Piperidin-1-yl-ethoxy)-phenylamine

HRID 898524Notes

Reaction equation

HRID 898524 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10](Cl)[CH:9]=1.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C(#N)C>[N:19]1([CH2:18][CH2:17][O:14][C:11]2[CH:12]=[CH:13][C:8]([NH2:7])=[CH:9][CH:10]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 748271-(2-Chloroethyl)piperidineHCID 775784-Amino-2-chlorophenol

Product 1

HCID 30160254-(2-Piperidin-1-yl-ethoxy)-phenylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

15.4 g (111.00 mmol) of potassium carbonate was added to a solution of 4.0 g (27.86 mmol) of 4-amino-2-chlorophenol and 5.1 g (27.86 mmol) of 1-(2-chloro-ethyl)-piperidine in 50 mL acetonitrile and the mixture was stirred for 48 hours at RT. The solvent was evaporated off i. vac., the residue was combined with water and the aqueous phase was exhaustively extracted with EtOAc. The combined org. extracts were washed with water, dried over magnesium sulphate, evaporated down i. vac. and the residue was purified by column chromatography (silica gel, dichloromethane/MeOH/conc. aqueous ammonia 90:10:1).

Workup

  1. customThe solvent was evaporated off i
  2. extractionthe aqueous phase was exhaustively extracted with EtOAc
  3. washextracts were washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated down i
  6. customand the residue was purified by column chromatography (silica gel, dichloromethane/MeOH/conc. aqueous ammonia 90:10:1)

Sources & evidence

ORD record
ord-9ff1f5c11f9f45ccbee9c2d8612370b8
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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