Potassium Hydroxide → 4-[3-(4-Carbamoylphenoxy)-1-pyrrolidinyl]pyridine

HRID 427458

Reaction equation

HRID 427458 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][CH:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH2:9]2)=[CH:5][CH:4]=1)#[N:2].[OH-:21].[K+]>C(O)(C)(C)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH2:9]2)=[CH:19][CH:20]=1)(=[O:21])[NH2:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 183570874-[3-(4-Cyanophenoxy)-1-pyrrolidinyl]pyridine

Product 1

HCID 183571004-[3-(4-Carbamoylphenoxy)-1-pyrrolidinyl]pyridineYield 57.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 4-[3-(4-cyanophenoxy)-1-pyrrolidinyl]pyridine (269 mg) and powdered potassium hydroxide (568 mg) in t-butanol (10 ml), under an atmosphere of argon, was heated under reflux for 18 hours. The mixture was filtered hot. The filtercake was washed with water and ethanol to give 4-[3-(4-carbamoylphenoxy)-1-pyrrolidinyl]pyridine (166 mg) as a colourless solid, mp 298-300° C.

Workup

  1. temperatureunder an atmosphere of argon, was heated
  2. temperatureunder reflux for 18 hours
  3. filtrationThe mixture was filtered hot
  4. washThe filtercake was washed with water and ethanol

Sources & evidence

ORD record
ord-1c442b2f30054d8ab9cea61c32b9e4d3
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Linked notes

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