Water → HCID 86707867, compound

HRID 922460Notes

Reaction equation

HRID 922460 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5]O.[H-].[Na+].F[C:10]1[CH:11]=[C:12]([CH:20]([NH:22][CH:23]2[CH2:25][CH2:24]2)[CH3:21])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1.O>CN(C)C=O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:10]1[CH:11]=[C:12]([CH:20]([NH:22][CH:23]2[CH2:25][CH2:24]2)[CH3:21])[CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 741163-Methoxy-1-propanolHCID 86707868HCID 86707868, compound

Product 1

HCID 86707867HCID 86707867, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-methoxy-1-propanol (0.14 mL) in N,N-dimethylformamide (3.0 mL) was added 60% oil-based sodium hydride (97 mg), and the mixture was stirred at room temperature for 10 minutes. Then, thereto was added dropwise a solution of N-{1-[3-fluoro-5-(trifluoromethyl)phenyl]ethyl}cyclopropylamine (300 mg) in N,N-dimethylformamide (1.0 mL), and the mixture was heated to stir at 40° C. for 4 hours. After cooling to room temperature, thereto was added water, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1→2/3) to give N-{1-[3-(3-methoxypropyl)-5-(trifluoromethyl)phenyl]ethyl}cyclopropanamine [REx(31-1)] (227 mg) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. stirringto stir at 40° C. for 4 hours
  3. temperatureAfter cooling to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was sequentially washed with water and saturated saline
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1→2/3)

Sources & evidence

ORD record
ord-97c6ff78c0fd48a294347c2b339f5486
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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