Dimethylformamide → N-isopropyl-7-(4-fluorophenyl)-7-(2-hydroxy-3,5,6-trimethylphenyl)heptane amide

HRID 373377Notes

Reaction equation

HRID 373377 reaction equation
CN(C)C=O.S(Cl)(Cl)=O.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:26]2[C:31]([CH3:32])=[C:30]([CH3:33])[CH:29]=[C:28]([CH3:34])[C:27]=2[OH:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=O)=[CH:13][CH:12]=1.[CH:36]([NH2:39])([CH3:38])[CH3:37]>ClCCl.C(N(CC)CC)C>[CH:36]([NH:39][C:23](=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:17]([C:14]1[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=1)[C:26]1[C:31]([CH3:32])=[C:30]([CH3:33])[CH:29]=[C:28]([CH3:34])[C:27]=1[OH:35])([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6363IsopropylamineHCID 24386Thionyl ChlorideHCID 15125097HCID 15125097, compound

Product 1

HCID 15125121N-isopropyl-7-(4-fluorophenyl)-7-(2-hydroxy-3,5,6-trimethylphenyl)heptane amide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a mixture of dichloromethane (10 ml) and dimethylformamide (0.43 ml) was added thionyl chloride (0.24 ml) at -10° C. and the mixture was stirred at the same temperature for 20 minutes. To this solution was added a solution of 7-(4-fluorophenyl)-7-(2-hydroxy-3,5,6-trimethylphenyl)heptanoic acid (1.0 g) in dichloromethane (5 ml) and the mixture was stirred at the same temperature for 1 hour. Isopropylamine (0.48 ml) and triethylamine (1.1 ml) were added and the temperature was raised slowly to room temperature. The reaction mixture was stirred at room temperature for 1 hour and washed in turn with 1N hydrochloric acid, water, aqueous sodium hydrogen carbonate, water and saturated saline and dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography and the resulting crystals were recrystallized from isopropyl ether to obtain N-isopropyl-7-(4-fluorophenyl)-7-(2-hydroxy-3,5,6-trimethylphenyl)heptane amide (0.64 g) (Compound 7). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. stirringThe reaction mixture was stirred at room temperature for 1 hour
  3. washwashed in turn with 1N hydrochloric acid, water, aqueous sodium hydrogen carbonate, water and saturated saline
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe resulting crystals were recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-7e693f5b9dae45b596c199a474dea496
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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