Cyclohexanecarboxylic acid → HCID 47041879, compound

HRID 397043Notes

Reaction equation

HRID 397043 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH2:8].[CH:12]1([C:18](O)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][NH:8][C:18]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:19])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 7413Cyclohexanecarboxylic acidHCID 748663-MethoxyphenethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 47041879HCID 47041879, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-methoxyphenethylamine (1.000 g, 6.61 mmol), cyclohexanecarboxylic acid (0.847 g, 6.61 mmol), 1-hydroxybenzotriazole hydrate (1.340 g, 9.92 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.330 g, 6.94 mmol) in anhydrous CH2Cl2 (20 ml) was stirred at 0° C. under N2 for 1 hr, then warmed to rt and stirred at rt for 18 hr. The reaction mixture was washed sequentially with 1M NaOH (10 ml), 1M HCl (10 ml), and H2O (10 ml), then dried over MgSO4 and concentrated in vacuo to give 1.301 g of off-white solid. Purification by flash chromatography, eluting with hexane:EtOAc (6:4) gave 1.107 g (64% yield) of white solid.

Workup

  1. temperaturewarmed to rt
  2. stirringstirred at rt for 18 hr
  3. washThe reaction mixture was washed sequentially with 1M NaOH (10 ml), 1M HCl (10 ml), and H2O (10 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01d0281f9a934736a192b44b1342dfe2
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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