HCID 57608455, compound → HCID 57956772, compound

HRID 1021110Notes

Reaction equation

HRID 1021110 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:11]#[C:12][CH:13]([OH:17])[CH:14]([CH3:16])[CH3:15])[CH:8]=[CH:9][CH:10]=1>CCO>[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][CH:13]([OH:17])[CH:14]([CH3:15])[CH3:16])[CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 1

HCID 57608455HCID 57608455, compound

Product 1

HCID 57956772HCID 57956772, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(3-(2-Aminoethoxy)phenyl)-4-methylpent-1-yn-3-ol (0.56 g, 2.4 mmol) in EtOH (30 mL) was degassed and purged with nitrogen. To this was added Pd on C (0.05 g, 10%). The flask was evacuated and purged with hydrogen thrice. This suspension was then stirred at room temperature under hydrogen balloon for overnight. The reaction mixture was filtered through a pad of Celite and the filter cake was washed with ethanol. The filtrate was concentrated to afford Example 1. Yield (0.38, 66%): 1H NMR (400 MHz, DMSO-d6) δ 7.14-7.18 (m, 1H), 6.71-6.76 (m, 3H), 3.91 (t, J=5.6 Hz, 2H), 3.12-3.17 (m, 1H), 2.89 (t, J=5.6 Hz, 2H), 2.65-2.73 (m, 1H), 2.46-2.50 (m, 1H), 1.46-1.64 (m, 3H), 0.8 (t, J=5.6 Hz, 2H). 13C NMR (100 MHz, DMSO-d6) δ 159.0, 144.8, 129.7, 121.1, 115.0, 112.0, 74.2, 69.6, 41.1, 36.2, 33.7, 32.4, 19.4, 18.0. MS: 238 [M+1]+.

Workup

  1. custompurged with nitrogen
  2. additionTo this was added Pd on C (0.05 g, 10%)
  3. customThe flask was evacuated
  4. custompurged with hydrogen thrice
  5. filtrationThe reaction mixture was filtered through a pad of Celite
  6. washthe filter cake was washed with ethanol
  7. concentrationThe filtrate was concentrated
  8. customto afford Example 1
  9. customYield (0.38, 66%)

Sources & evidence

ORD record
ord-e4f6752acf0c426ba08b68ea24c76228
Source dataset
uspto-grants-2014_05
Patent number
US08716529B2

Reaction notes

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