Ammonium Hydroxide → HCID 25166542, compound

HRID 2172735Notes

Reaction equation

HRID 2172735 reaction equation
FC(F)(F)C([NH:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[C:16][C:17]([OH:24])([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:10]=1)=O.[NH4+].[OH-]>CO>[NH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]#[C:16][C:17]([OH:24])([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14923Ammonium Hydroxide2×HCID 86635851HCID 86635851, compound

Product 1

HCID 25166542HCID 25166542, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-(3-(3-(3-hydroxy-3-propylhex-1-ynyl)phenyl)propyl)acetamide (2.6 g, 7.0 mmol) in MeOH (50 mL) was added concentrated aqueous NH4OH (ca. 25 mL) and the solution was stirred at room temperature overnight. More concentrated aqueous NH4OH (5 mL) was added and the mixture was stirred overnight. The volatiles were removed by concentration under reduced pressure and the residue was extracted twice with EtOAc. The organic solution was washed with water and brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (0 to 20% (20% 7M NH3 in MeOH-EtOAc)-EtOAc gradient) gave 4-((3-(3-aminopropyl)phenyl)ethynyl)heptan-4-ol as a clear oil. Yield (1.58 g, 83%): 1H NMR (400 MHz, DMSO-d6) δ 7.14-7.26 (m, 4H), 5.12 (s, 1H), 2.56 (t, J=7.2 Hz, 2H), 2.47 (t obs, J=7.2 Hz, 2H), 1.42-1.63 (m, 12H), 0.90 (t, J=7.2 Hz, 6H).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe volatiles were removed by concentration under reduced pressure
  3. extractionthe residue was extracted twice with EtOAc
  4. washThe organic solution was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (0 to 20% (20% 7M NH3 in MeOH-EtOAc)-EtOAc gradient)

Sources & evidence

ORD record
ord-6415c14c2ff14cf38fbce748b83f86ce
Source dataset
uspto-grants-2015_06
Patent number
US09056849B2

Reaction notes

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