3-Pyridinebutanoic acid → 4-Diphenylmethyl-1-[1-oxo-4-(3-pyridinyl)butyl]piperidine

HRID 1249568노트

반응식

HRID 1249568 반응식
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])[CH:21]=1>CN(C)C=O.C(N(CC)CC)C.ClCCl>[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:9][CH2:10][N:11]([C:29](=[O:30])[CH2:28][CH2:27][CH2:26][C:22]3[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 2

HCID 1143-Pyridinebutanoic acidHCID 882784-Benzhydrylpiperidine

생성물 1

HCID 202234374-Diphenylmethyl-1-[1-oxo-4-(3-pyridinyl)butyl]piperidine수율 88.3%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매2회HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

A mixture of 2.0 g of 4-diphenylmethylpiperidine in 5 mL of dimethylformamide and 4.2 mL of triethylamine was treated at 0° C. with a solution composed of 5 mL of dimethylformamide and the acid chloride prepared from 2.0 g of 3-pyridine butanoic acid. After 15 minutes the mixture was diluted with dichloromethane, filtered and evaporated to dryness. The residue was partitioned between toluene and 1N sodium hydroxide and the organic layer was washed with brine, dried over sodium sulfate and evaporated to give 3.3 g of crude oil. Purification was accomplished by chromatography on a Waters Prep 500 HPLC using silica gel columns and eluting with 98:2 ethyl acetate-triethylamine. The product consisted of a colorless oil which was dried under vacuum at 70° C. to give 2.8 g (86%) of 4-diphenylmethyl-1-[1-oxo-4-(3-pyridinyl)butyl]piperidine, 0.1 molar ethylacetate solvate. Analysis Calculated for C27H30N2O.O.1C4H8O 2 : C, 80.79; H, 7.62; N, 6.88. Found: C, 80.91; H, 7.57; N, 6.81.

후처리

  1. additionwas treated at 0° C. with a solution
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customThe residue was partitioned between toluene and 1N sodium hydroxide
  5. washthe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto give 3.3 g of crude oil
  9. customPurification
  10. washeluting with 98:2 ethyl acetate-triethylamine
  11. customwas dried under vacuum at 70° C.

출처 및 근거

ORD 기록
ord-c3625b755fe545eaaa09b02d8d1f106a
출처 데이터셋
uspto-grants-1986_12
특허 번호
US04632925

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