Sodium Iodide → HCID 67776051, compound

HRID 1408291Notes

Reaction equation

HRID 1408291 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([O:7][C:8]1([CH2:13][CH3:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:6].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C(C)=CC=CC=1C.[I-].[Na+]>O>[C:16]1([NH:15][CH2:2][CH2:3][CH2:4][C:5]([O:7][C:8]2([CH2:13][CH3:14])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:6])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6115AnilineHCID 79372,6-LutidineHCID 67776007HCID 67776007, compound

Product 1

HCID 67776051HCID 67776051, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a nitrogen atmosphere, a mixture of 15 g of 1-ethylcyclopentyl 4-chlorobutyrate, 19 g of aniline, 7.3 g of 2,6-lutidine, and 1.5 g of sodium iodide was heated at 80° C. and stirred for 36 hours at the temperature. The reaction mixture was cooled, after which 15 g of water was added dropwise to quench the reaction. This was followed by ordinary aqueous work-up and vacuum distillation (135° C./13 Pa), recovering 14 g (yield 76%) of 1-ethylcyclopentyl 4-(phenylamino)butyrate.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customto quench
  3. customthe reaction
  4. distillationThis was followed by ordinary aqueous work-up and vacuum distillation (135° C./13 Pa)

Sources & evidence

ORD record
ord-a28df9ee792f4f07bd08a7ce6916535b
Source dataset
uspto-grants-2014_12
Patent number
US08921026B2

Reaction notes

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