Potassium Carbonate → 2-Bromo-N-cyclohexyl-N-cyclopropyl-acetamide

HRID 884346Notes

Reaction equation

HRID 884346 reaction equation
Cl.[CH:2]1([NH:8][CH:9]2[CH2:11][CH2:10]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[Br:18][CH2:19][C:20](Br)=[O:21]>C(Cl)Cl.O>[Br:18][CH2:19][C:20]([N:8]([CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)[CH:9]1[CH2:11][CH2:10]1)=[O:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 44118464N-cyclopropylcyclohexanamine hydrochloride

Product 1

HCID 685626022-Bromo-N-cyclohexyl-N-cyclopropyl-acetamideYield 71.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To an ice cooled mixture of 1.054 g (6 mmol) of N-cyclohexyl-N-cyclopropylamine hydrochloride, 2.07 g (15 mmol) of potassium carbonate in 15 ml of methylene chloride and 15 ml of water was added 1.2 g (6 mmol) of bromoacetyl bromide. Then the reaction mixture was stirred at RT for 20 h. The organic phase washed with water, dried over sodium sulphate and evaporated to dryness to give 1.33 g of crude compound. Flash chromatography using DCM as eluant afforded 1.12 g of the desiderated compound as colorless oil.

Workup

  1. washThe organic phase washed with water
  2. dry with materialdried over sodium sulphate
  3. customevaporated to dryness
  4. customto give 1.33 g of crude compound

Sources & evidence

ORD record
ord-a26b013059cb454c96d4969ff331d6ed
Source dataset
uspto-grants-2012_08
Patent number
US08242107B2

Reaction notes

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