Hydrochloric Acid → 4-(2-Methylphenyl)-1-[3-(5,6,7,8-tetrahydronaphth-1-yloxy)-prop1-yl]-piperazine hydrochloride

HRID 268398ノート

反応式

HRID 268398 の反応式
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][Cl:36])[CH2:29][CH2:28]1.Cl>CCOCC.C(C(C)=O)C>[ClH:36].[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:28][CH2:29][N:30]([CH2:33][CH2:34][CH2:35][O:11][C:1]2[C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[CH:4]=[CH:3][CH:2]=2)[CH2:31][CH2:32]1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 682585,6,7,8-Tetrahydro-1-naphtholHCID 2336711-(3-Chloropropyl)-4-(2-methylphenyl)piperazine

生成物 1

HCID 215516544-(2-Methylphenyl)-1-[3-(5,6,7,8-tetrahydronaphth-1-yloxy)-prop1-yl]-piperazine hydrochloride収率 72%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6569Methyl Ethyl Ketone溶媒2 回

実験手順

A mixture of 8.15 g. (55 mMole) 5,6,7,8-tetrahydro-1-naphthol, 7.60 g. (55 mMole) powdered dry potassium carbonate and 100 ml. anhydrous methyl ethyl ketone was heated under reflux for 2 hours and then cooled somewhat. 0.2 g. potassium iodide were added thereto and a solution of 12.64 g. (50 mMole) 4-(2-methylphenyl)-1-(3-chloropropyl)-piperazine in 50 ml. anhydrous methyl ethyl ketone then added dropwise, whereafter the reaction mixture was heated under reflux for a further 16 hours. After filtering with suction, the filter cake obtained was washed with acetone. The combined organic filtrates were evaporated in a vacuum, the oily evaporation residue was taken up in chloroform and the chloroform solution was extracted several times with a dilute aqueous solution of sodium hydroxide and then with distilled water. After drying and evaporating in a vacuum, there was obtained an oily product which was dissolved in ether and treated with dry hydrogen chloride. The precipitated 4-(2-methylphenyl)-1-[3-(5,6,7,8-tetrahydronaphth-1-yloxy)-prop1 -yl]-piperazine hydrochloride thus obtained was filtered off with suction, washed with some ether and finally with alcohol to which some concentrated hydrochloric acid had been added. The yield was 72% of theory and the product has a melting point of 243°-244°C.

後処理

  1. additionA mixture of 8.15 g
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled somewhat
  4. temperaturewas heated
  5. temperatureunder reflux for a further 16 hours
  6. filtrationAfter filtering with suction
  7. customthe filter cake obtained
  8. washwas washed with acetone
  9. customThe combined organic filtrates were evaporated in a vacuum
  10. extractionthe chloroform solution was extracted several times with a dilute aqueous solution of sodium hydroxide
  11. customAfter drying
  12. customevaporating in a vacuum
  13. customthere was obtained an oily product which

出典と根拠

ORDレコード
ord-be1716db50c0446cbabb13f734a1edd9
出典データセット
uspto-grants-1976_03
特許番号
US03947446

反応ノート

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