Triethylamine → HCID 178483572, compound

HRID 2209818Notes

Reaction equation

HRID 2209818 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.O[CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C@H:24]2[CH2:29][CH2:28][C@H:27]([NH:30][CH3:31])[CH2:26][CH2:25]2)=[C:20](CNC)[CH:19]=1.C([N:37]([CH2:40]C)CC)C.[C:42](OCC)(=[O:44])C>C(Cl)Cl>[OH:44][CH2:42][CH2:15][CH2:16][CH:17]([NH:37][CH3:40])[C:18]1[CH:19]=[CH:20][C:21]([C@H:24]2[CH2:25][CH2:26][C@H:27]([N:30]([CH3:31])[C:7](=[O:8])[C:6]3[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=3)[CH2:28][CH2:29]2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 178482764HCID 178482764, compound

Product 1

HCID 178483572HCID 178483572, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Whilst cooling with ice, a solution of 145 mg (0.69 mMol) of 4-trifluoromethylbenzoylchloride in a little methylene chloride is added dropwise to 200 mg (0.69 mMol) of trans-4-[4-(3-hydroxypropyl)-methylaminomethylphenyl]-N-methylcyclohexylamine and 0.1 ml (0.73 mMol) of triethylamine in 3 ml of methylene chloride and the resulting mixture is stirred for 2 hours at ambient temperature. After the reaction mixture has been diluted with ethyl acetate it is washed with water, 1N sodium hydroxide solution and saturated saline solution, then dried and evaporated down. The residue is purified by column chromatography (alumina, ethyl acetate/petroleum ether=1:1, v:v). 130 mg (40.8% of theory) of the title compound are obtained, melting point 87°-89° C.

Workup

  1. temperatureWhilst cooling with ice
  2. washis washed with water, 1N sodium hydroxide solution and saturated saline solution
  3. customdried
  4. customevaporated down
  5. customThe residue is purified by column chromatography (alumina, ethyl acetate/petroleum ether=1:1, v:v)

Sources & evidence

ORD record
ord-961c8faf41e64109b7a6c347cc217483
Source dataset
uspto-grants-1995_10
Patent number
US05455273

Reaction notes

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