Methylparaben → 4-(2-Piperidinoethoxy)benzoic acid hydrochloride

HRID 1421371

反応式

HRID 1421371 の反応式
FC(F)(F)CS([Cl:7])(=O)=O.[N:10]1([CH:16](O)[CH3:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].[OH:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32]C)=[O:31])=[CH:28][CH:27]=1>C(Cl)Cl.C(OCCCCC)(=O)C>[ClH:7].[N:10]1([CH2:16][CH2:17][O:25][C:26]2[CH:35]=[CH:34][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

参加物

7

反応物 4

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 30305411-(Piperidin-1-yl)ethanol

生成物 1

HCID 57438354-(2-Piperidinoethoxy)benzoic acid hydrochloride収率 93.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 12348Amyl Acetate溶媒

反応条件

温度
140 °C

実験手順

Into a 50 ml round bottom flask is placed 4.93 g (27.0 mmol) of 2,2,2-trifluoroethanesulfonyl chloride and 25 ml of methylene chloride. The resulting solution is cooled with an ice bath as 3.22 g (24.9 mmol) of 1-piperidinoethanol in 7 ml of methylene chloride is added dropwise. After the addition is complete, the ice bath is removed and the resulting slurry is stirred for about 12 hours. The reaction mixture is concentrated on a rotary evaporator to yield a waxy residue. The solid residue is slurried in 45 ml of amyl acetate and then potassium carbonate (5.50 g, 39.9 mmol) and methyl 4-hydroxybenzoate (2.26 g, 14.8 mmol) are added. The resulting mixture is heated to 140° C. for 2 hours. The reaction mixture is cooled to room temperature and washed twice with water and the organic layer is extracted with 10.5 ml of 8 N hydrochloric acid. The aqueous layer is heated at gentle reflux for 4 hours. The resulting slurry is cooled to 50° C. and 11 ml of acetone is added. The slurry is cooled to 0-5° C. and stirred for 1 hour. The product is filtered, washed with cold acetone, and dried at 50° C. in vacuo to yield 3.94 g of product, (90%). 1H NMR. HPLC 96.9%. TRS 2.78%.

後処理

  1. customInto a 50 ml round bottom flask is placed
  2. additionis added dropwise
  3. additionAfter the addition
  4. customthe ice bath is removed
  5. concentrationThe reaction mixture is concentrated on a rotary evaporator
  6. customto yield a waxy residue
  7. temperatureThe reaction mixture is cooled to room temperature
  8. washwashed twice with water
  9. extractionthe organic layer is extracted with 10.5 ml of 8 N hydrochloric acid
  10. temperatureThe aqueous layer is heated
  11. temperatureat gentle reflux for 4 hours
  12. temperatureThe resulting slurry is cooled to 50° C.
  13. addition11 ml of acetone is added
  14. temperatureThe slurry is cooled to 0-5° C.
  15. stirringstirred for 1 hour
  16. filtrationThe product is filtered
  17. washwashed with cold acetone
  18. customdried at 50° C. in vacuo

出典と根拠

ORDレコード
ord-a468fc0052b347668176a6bfc4de27e6
出典データセット
uspto-grants-2000_06
特許番号
US06075146

関連ノート

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