Triethylamine → 2-[(Dimethylamino)(phenyl)methyl]cyclohexyl 4-(trifluoromethyl)benzoate hydrochloride

HRID 1596033Notes

Reaction equation

HRID 1596033 reaction equation
FC(F)(F)C1C=CC(C([Cl:9])=O)=CC=1.C(N(CC)CC)C.CN(C(C1C=CC=CC=1)C1CCCCC1O)C.[OH-].[K+].[CH3:40][N:41]([CH:43]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[CH:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH:45]1[O:50][C:51](=[O:62])[C:52]1[CH:57]=[CH:56][C:55]([C:58]([F:61])([F:60])[F:59])=[CH:54][CH:53]=1)[CH3:42]>C(Cl)Cl>[ClH:9].[CH3:42][N:41]([CH:43]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[CH:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH:45]1[O:50][C:51](=[O:62])[C:52]1[CH:53]=[CH:54][C:55]([C:58]([F:61])([F:60])[F:59])=[CH:56][CH:57]=1)[CH3:40]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 9846162[2-(Dimethylaminophenyl-methyl)cyclohexyl]4-trifluoromethylbenzoateHCID 112647962-(Dimethylaminophenylmethyl)cyclohexanol

Product 1

HCID 98461612-[(Dimethylamino)(phenyl)methyl]cyclohexyl 4-(trifluoromethyl)benzoate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.34 g (6.43 mmole) of 4-(trifluoromethyl)benzoyl chloride were dissolved in 4 ml methylene chloride, and 870 mg (8.57 mmole) triethylamine were added at −10° C. (methanol/ice cooling bath). 1.0 g (4.29 mmole) 2-(dimethylaminophenylmethyl)cyclohexanol, dissolved in 2 ml methylene chloride, was then added dropwise, and the mixture was subsequently stirred for 15 hours. For working up, 2 ml potassium hydroxide solution (0.5 N) were added and the organic phase was separated, dried over sodium sulfate, filtered and concentrated on a rotary evaporator (500 to 10 mbar). 1.7 g of crude base were obtained. 877 mg of the hydrochloride of [2-(dimethylaminophenyl-methyl)cyclohexyl]4-trifluoromethylbenzoate (34% of theoretical) with a melting point above 230° C. were obtained from the crude base in accordance with Example 1 (4th stage) using chloro-trimethylsilane/water in 2-butanone.

Workup

  1. additionwas then added dropwise
  2. customthe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator (500 to 10 mbar)
  6. custom1.7 g of crude base were obtained

Sources & evidence

ORD record
ord-04793bf9d6f4427f997206c7bcbd397e
Source dataset
uspto-grants-2001_09
Patent number
US06288278B1

Reaction notes

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