Dimethylamine → HCID 67404297, compound

HRID 1186402Notes

Reaction equation

HRID 1186402 reaction equation
[F:1][C:2]([F:14])([F:13])[CH:3]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[OH:4].[CH3:15][NH:16][CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(#N)C.O1CCCC1.C(OCC)(=O)C.C(O)(=O)C>[CH3:15][N:16]([CH2:9][C:8]1[CH:11]=[CH:12][C:5]([CH:3]([OH:4])[C:2]([F:14])([F:13])[F:1])=[CH:6][CH:7]=1)[CH3:17]

Participants

9

Reactant 4

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 84734005HCID 84734005, compound

Product 1

HCID 67404297HCID 67404297, compoundYield 85%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(2,2,2-Trifluoro-1-hydroxyethyl)benzaldehyde (295 mg, 1.4 mmol) obtained in Step 1 of Reference Example 8-70 was dissolved in acetonitrile (15 mL). To this, dimethylamine (a 1.0 mol/L solution in tetrahydrofuran, 7.2 mL, 14 mmol) and acetic acid (0.83 mL) were added and the mixture was stirred at room temperature for 30 minutes. To this, sodium triacetoxyborohydride (918 mg, 4.3 mmol) was added and the mixture was stirred at room temperature for 4 hours. Then, an aqueous sodium bicarbonate solution was added to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was subjected to slurry purification using a mixed solvent of diisopropyl ether and hexane. Further, purification by silica gel column chromatography (hexane/ethyl acetate=1/0 to 2/1) was performed to give 1-{4-[(dimethylamino)methyl]phenyl}-2,2,2-trifluoroethanol (Compound ER) (284 mg, yield: 85%).

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. washby washing with brine
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. customThe solvent was evaporated off under reduced pressure
  5. custompurification
  6. customFurther, purification by silica gel column chromatography (hexane/ethyl acetate=1/0 to 2/1)

Sources & evidence

ORD record
ord-52466041c9444446ac2a45922354f127
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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