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

HRID 459663ノート

反応式

HRID 459663 の反応式
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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b1731f5445bf4c4fbc978c6446ed76fc
出典データセット
uspto-grants-2007_03
特許番号
USRE039530E1

反応ノート

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