1,1-Dichloroethane → Fentanyl

HRID 1948977

反応式

HRID 1948977 の反応式
[NH:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)C.[C:26](Cl)(=[O:29])[CH2:27][CH3:28]>>[CH3:28][CH2:27][C:26]([N:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:29]

参加物

4

反応物 3

HCID 63651,1-DichloroethaneHCID 62324Propionyl chlorideHCID 88890N-phenyl-1-(2-phenylethyl)-4-piperidinamine

生成物 1

HCID 3345Fentanyl

実験手順

A solution of 5.5 parts (w/w) of 4-anilino-N-phenethyl-piperidine preferably 1 to 3 parts in 5 to 15 parts (w/w) of dichloroethane preferably 8 to 12 parts was taken in a two neck round bottom flask fitted with a reflux condenser, pressure equalizing funnel and calcium chloride guard tube. To this stirred solution, 2 to 20 parts 9 w/w) of propionyl chloride preferably 5 to 15 parts was added drop wise through pressure equalizing funnel. After 2 to 6 hrs, preferably 4 to 5 hrs stirring at room temperature, the reaction mixture was washed with 20% sodium hydroxide solution. The washings were extracted with 2×50 parts, preferably 65 to 70 parts dichloroethane. The combined organic phase was dried over sodium sulphate and concentrated to give fentanyl. The crude compound was recrystallised from petroleum ether (60 to 80° C.) to give colourless crystals of pure fentanyl having mp 82 to 83° C.

後処理

  1. customfitted with a reflux condenser
  2. washthe reaction mixture was washed with 20% sodium hydroxide solution
  3. extractionThe washings were extracted with 2×50 parts, preferably 65 to 70 parts dichloroethane
  4. dry with materialThe combined organic phase was dried over sodium sulphate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-766d0799bdea45eeaf2062bd98711cc5
出典データセット
uspto-grants-2013_03
特許番号
US08399677B2

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