4-Aminophenethyl alcohol → HCID 11551674, compound

HRID 2264233Notes

Reaction equation

HRID 2264233 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12]([C:19]3[CH:24]=[CH:23][N:22]=[C:21](Cl)[N:20]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][OH:35])=[CH:29][CH:28]=1>COC(O)C>[NH:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C:12]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][OH:35])=[CH:29][CH:28]=3)[N:20]=2)=[CH:11]1

Participants

4

Reactant 2

HCID 669044-Aminophenethyl alcoholHCID 59596028HCID 59596028, compound

Product 1

HCID 11551674HCID 11551674, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of compound 1f (4.00 g) and 2-(4-aminophenyl)-ethanol (2.96 g) in 1-methoxyethanol (30 mL) was heated at 160° C. for 17 hrs in a pressure tube. The mixture was then cooled, quenched with water and extracted with mixed THF and ethyl acetate. The combined organic phase was washed with brine and concentrated. The residue was subjected to silica column and eluted with 2-6% methanol in dichloromethane to give compound 1 (3.01 g, yield 84%) as a white solid. 1H NMR (400 MHz, CD3OD) δ 8.89 (d, J=8.0 Hz, 1H), 8.26 (dd, J=5.2 Hz, 2.0 Hz, 2H), 8.22 (s, 1H), 7.59 (m, 2H), 7.20 (m, 4H), 3.78 (t, J=7.2 Hz, 2H), 2.83 (t, J=7.2 Hz, 2H). MS (ESI) m/z: 332 (M+H)+.

Workup

  1. temperatureThe mixture was then cooled
  2. customquenched with water
  3. extractionextracted with mixed THF and ethyl acetate
  4. washThe combined organic phase was washed with brine
  5. concentrationconcentrated
  6. washeluted with 2-6% methanol in dichloromethane

Sources & evidence

ORD record
ord-c79763573cd14c409f3fb7cd934530de
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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