Cyclohexylamine → Ammonia

HRID 843155Notes

Reaction equation

HRID 843155 reaction equation
C(O[C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH:18]([OH:24])[CH2:19][NH:20][CH:21]([CH3:23])[CH3:22])[C:9]=2[C:10]=1[CH3:11])=[O:5])C.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C(OCC)(=O)C>[NH3:20].[CH:25]1([NH:31][C:4]([C:6]2[O:7][C:8]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH:18]([OH:24])[CH2:19][NH:20][CH:21]([CH3:22])[CH3:23])[C:9]=3[C:10]=2[CH3:11])=[O:5])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 7965CyclohexylamineHCID 489104HCID 489104, compound

Product 2

HCID 222AmmoniaYield 25%HCID 53840807HCID 53840807, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(2-hydroxy-3-isopropylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (A. N. Grinev et al., Otkrytiya, Izobret. 1986, (43), 275) (10 mg) and cyclohexylamine (50 μl) was heated at 175° C. for 11 hours. The reaction mixture was dissolved in ethyl acetate and washed with 0.1 N HCl solution and water. The organic solvent was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by preparative thin layer chromatography (using dichloromethane:MeOH:ammonia solution (25-28%)=10:1:0.2 as a developing solvent) to give 4-(2-hydroxy-3-isopropylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid cyclohexylamide (7 mg) as a white powder. FAB-MS: m/z 389 (MH+); 1H-NMR (CDCl3): δ 1.10 (6H, d, J=6 Hz), 1.20-2.04 (10H, m), 2.78 (3H, s), 2.83 (1H, m), 2.87 (1H, dd, J1=12.5 Hz, J2=6 Hz), 2.97 (1H, dd, J1=12.5 Hz, J2=3 Hz), 3.97 (1H, m), 4.08 (3H, m), 6.45 (1H, br d, J=8 Hz), 6.64 (1H, d, J=8 Hz), 7.04 (1H, d, J=8 Hz), 7.27 (1H, t, J=8 Hz).

Workup

  1. washwashed with 0.1 N HCl solution and water
  2. dry with materialThe organic solvent was dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by preparative thin layer chromatography (

Sources & evidence

ORD record
ord-eefdcfdb0bd84dbcb9216733fb00d4b2
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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