Triethylamine → 2-Isopropyl-5-methyl-cyclohexanecarboylic acid [2-(2-bromo-phenyl)-ethyl]-amide

HRID 1914928Notes

Reaction equation

HRID 1914928 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][NH2:6].C(N(CC)CC)C.[CH:18]1([CH3:30])[CH2:23][CH2:22][CH:21]([CH:24]([CH3:26])[CH3:25])[CH:20]([C:27](Cl)=[O:28])[CH2:19]1>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][NH:6][C:27]([CH:20]1[CH2:19][CH:18]([CH3:30])[CH2:23][CH2:22][CH:21]1[CH:24]([CH3:26])[CH3:25])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27340912-BromophenethylamineHCID 13734319Cyclohexanecarbonyl chloride, 5-methyl-2-(1-methylethyl)-

Product 1

HCID 668315152-Isopropyl-5-methyl-cyclohexanecarboylic acid [2-(2-bromo-phenyl)-ethyl]-amideYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 100 mL round bottom flask equipped with a stir bar was charged with CH2Cl2 (30 mL), 2-bromo-phenethylamine (1.0 g, 5.00 mmol) and triethylamine (684 μl, 5.05 mmol). The reaction solution was treated with menthoyl chloride (1.02 g, 5.05 mmol) in one portion and stirred at ambient temperature for 30 minutes. The reaction was diluted with CH2Cl2 (50 mL) and washed with water (3×100 mL). Organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a thick oil (1.8 g). Product was used for next step without purification.

Workup

  1. customA 100 mL round bottom flask equipped with a stir bar
  2. washwashed with water (3×100 mL)
  3. dry with materialOrganic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b4b2000b205488a84352b1f10fe629f
Source dataset
uspto-grants-2013_12
Patent number
US08614243B2

Reaction notes

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