Potassium Fluoride → HCID 19040910, 화합물

HRID 1683843노트

반응식

HRID 1683843 반응식
Cl.[F:2][C:3]([F:31])([F:30])[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)([OH:18])[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1.[CH2:32]([O:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42]Cl)=[CH:38][CH:37]=1)[C:33]#[CH:34].[F-].[K+]>>[CH2:32]([O:35][C:36]1[CH:37]=[CH:38][C:39]([CH2:42][N:15]2[CH2:16][CH2:17][CH:12]([C:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][C:3]([F:30])([F:2])[F:31])=[CH:10][CH:9]=3)([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:27])[F:28])=[CH:21][CH:20]=3)[OH:18])[CH2:13][CH2:14]2)=[CH:40][CH:41]=1)[C:33]#[CH:34]

참가 물질

4

반응물 3

HCID 522689Potassium FluorideHCID 107498961-(Chloromethyl)-4-(2-propyn-1-yloxy)benzeneHCID 19040925HCID 19040925, 화합물

생성물 1

HCID 19040910HCID 19040910, 화합물수율 64.7%

실험 절차

A stirred mixture of 0.8 gram (0,0016 mole) of 4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine hydrochloride, 0.3 gram (0.0016 mole) of 4-(2-propyn-1-yloxy)phenylmethyl chloride and 0.5 gram (0.0079 mole) of potassium fluoride on Celite® filter aid in 50 mL of acetonitrile was heated at reflux for about 1.3 hours. After this time 0.5 mL (excess) of triethylamine was added, and the reaction mixture became homogeneous. Upon completion of addition, the reaction mixture was heated at reflux for an additional 18 hours. After this time the reaction mixture was cooled, filtered, and the filtrate concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with mixtures of 10-70% diethyl ether in hexane as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.6 gram of N-[4-(2-propyn-1-yloxy)phenylmethyl]-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine. The NMR spectrum was consistent with the proposed structure.

후처리

  1. filtrationfilter aid in 50 mL of acetonitrile
  2. temperaturewas heated
  3. temperatureat reflux for about 1.3 hours
  4. additionAfter this time 0.5 mL (excess) of triethylamine was added
  5. additionUpon completion of addition
  6. temperaturethe reaction mixture was heated
  7. temperatureat reflux for an additional 18 hours
  8. temperatureAfter this time the reaction mixture was cooled
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under reduced pressure to a residue, which
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ef7f1dfe479f4571837407abd1975331
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639763

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