Morpholine → 3-[4-(1-t-Butyloxycarbonyl piperidin-4-yloxy)phenyl]-1-(morpholin-4-yl)prop-2-ene-1-one

HRID 520813노트

반응식

HRID 520813 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[CH:22][C:23]([OH:25])=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(OC(Cl)=O)C.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([CH:21]=[CH:22][C:23]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)=[O:25])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 900421133-[4-(1-t-Butyloxycarbonyl piperidin-4-yloxy)phenyl]prop-2-ene-1-oic acid

생성물 1

HCID 900429883-[4-(1-t-Butyloxycarbonyl piperidin-4-yloxy)phenyl]-1-(morpholin-4-yl)prop-2-ene-1-one수율 74.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
2.5 °C

실험 절차

To a stirred solution of 3-[4-(1-t-butyloxycarbonyl piperidin-4-yloxy)phenyl]prop-2-ene-1-oic acid (38 grams, 0.109 moles, obtained in above step) and triethylamine (38.4 mL, 0.273 moles) in dichloromethane (500 mL) was added ethylchloroformate (13.6 mL, 0.142 moles) at 0° C. The reaction mass was further stirred for 2 hours at 0-5° C. Morpholine (19.2 mL, 0.219 moles) was added to above mass at 0-5° C. and the resulting mixture were stirred for 2 hours. The progress of the reaction was monitored by thin layer chromatography. After completion of reaction, the mass was quenched by adding water (100 mL). Layers were separated and the organic layer was washed with brine solution (100 mL) and dried over sodium sulphate. The organic phase was concentrated under vacuum to obtain the crude residue, which was further purified by flash chromatography using methanol:triethylamine:chloroform in the ratio of 1:1:98 to afford the title compound (34 grams).

후처리

  1. stirringthe resulting mixture were stirred for 2 hours
  2. customAfter completion of reaction
  3. customthe mass was quenched
  4. additionby adding water (100 mL)
  5. customLayers were separated
  6. washthe organic layer was washed with brine solution (100 mL)
  7. dry with materialdried over sodium sulphate
  8. concentrationThe organic phase was concentrated under vacuum
  9. customto obtain the crude residue, which
  10. customwas further purified by flash chromatography

출처 및 근거

ORD 기록
ord-f2a8016aa5bd47fc8ae2da33a407c692
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328092B2

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