Methyl Ethyl Ketone → Ethyl 4-(2-Piperidinoethoxy)benzoate

HRID 989802

반응식

HRID 989802 반응식
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Cl.Cl[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>O.C(OCC)(=O)C.C(#N)C.C(N(CC)CC)C>[N:17]1([CH2:16][CH2:15][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

참가 물질

7

반응물 4

HCID 6569Methyl Ethyl KetoneHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochloride3회

생성물 1

HCID 9838504Ethyl 4-(2-Piperidinoethoxy)benzoate

시약·촉매·용매 2

HCID 962Water용매HCID 86586431Ethyl acetate acetonitrile triethylamine용매

반응 조건

온도
80 °C

실험 절차

A mixture of ethyl 4-hydroxybenzoate (8.31 g), 1-(2-chloroethyl)piperidine monohydrochloride (10.13 g), potassium carbonate (16.59 g), and methyl ethyl ketone (60 mL) was heated to 80° C. After one hour, the mixture was cooled to about 55° C. and treated with additional 1-(2-chloroethyl)piperidine mono-hydrochloride (0.92 g). The resulting mixture was heated to 80° C. The reaction was monitored by thin layer chromatography (TLC), using silicagel plates and ethyl acetate/acetonitrile/triethylamine (10:6:1, v/v). Additional portions of 1-(2-chloroethyl)piperidine hydrochloride are added until the starting 4-hydroxybenzoate ester is consumed. Upon complete reaction, the reaction mixture was treated with water (60 mL) and allowed to cool to room temperature. The aqueous layer was discarded and the organic layer concentrated in vacuo at 40° C. and 40 mm Hg. The resulting oil was used in the next step without further purification.

후처리

  1. temperaturethe mixture was cooled to about 55° C.
  2. temperatureThe resulting mixture was heated to 80° C
  3. customis consumed
  4. customUpon complete reaction
  5. temperatureto cool to room temperature
  6. concentrationthe organic layer concentrated in vacuo at 40° C.
  7. customThe resulting oil was used in the next step without further purification

출처 및 근거

ORD 기록
ord-8fa0472f1ff64ea1977bc2220ed9f73a
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458811B1

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