3-Fluorobenzyl chloride → [4-(3-Fluorobenzyloxy)-1-phenylcyclohexyl]dimethylamine

HRID 1349395ノート

反応式

HRID 1349395 の反応式
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.CC(C)([O-])C.[K+].[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Cl>CN(C)C=O>[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][O:9][CH:6]1[CH2:7][CH2:8][C:3]([N:2]([CH3:16])[CH3:1])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][CH2:5]1

参加物

5

反応物 3

HCID 99743-Fluorobenzyl chlorideHCID 111487094-Dimethylamino-4-phenylcyclohexanolHCID 23665647Potassium tert-butoxide

生成物 1

HCID 10308653[4-(3-Fluorobenzyloxy)-1-phenylcyclohexyl]dimethylamine収率 33.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2.00 g of 4-dimethylamino-4-phenylcyclohexanol were dissolved in 20 ml of dimethylformamide; 1.13 g of potassium tert.-butoxide were added and stirring was carried out for 45 minutes, before 1.45 g of 3-fluorobenzyl chloride were added dropwise in the course of 15 minutes. After stirring overnight, the mixture was added to 25 ml of ice-water and extracted repeatedly with ethyl acetate. The combined extracts were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The resulting crude product (2.71 g) was separated on silica gel with hexane/diethyl ether (V:V=1:1). 996 mg of [4-(3-fluorobenzyloxy)-1-phenylcyclohexyl]dimethylamine were obtained and, as described for Example 1, were converted into 720 mg of the corresponding hydrochloride with chlorotrimethylsilane and water in 2-butanone.

後処理

  1. additionwere added dropwise in the course of 15 minutes
  2. stirringAfter stirring overnight
  3. extractionextracted repeatedly with ethyl acetate
  4. washThe combined extracts were washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude product (2.71 g) was separated on silica gel with hexane/diethyl ether (V:V=1:1)

出典と根拠

ORDレコード
ord-f7c1e52511a543d8bdc6954b2607a3b7
出典データセット
uspto-grants-2007_05
特許番号
US07211694B2

反応ノート

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