Toluene → 1-[4-(Phenylmethoxy)phenyl]-4-[4-(trifluoromethoxy)phenoxy]piperidine

HRID 1039609노트

반응식

HRID 1039609 반응식
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1.Br[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:22][CH:21]=1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1([B-](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.O>[CH2:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([N:12]2[CH2:11][CH2:10][CH:9]([O:8][C:7]3[CH:15]=[CH:16][C:4]([O:3][C:2]([F:1])([F:17])[F:18])=[CH:5][CH:6]=3)[CH2:14][CH2:13]2)=[CH:21][CH:22]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

9

반응물 4

HCID 1140TolueneHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 161154394-[4-(Trifluoromethoxy)phenoxy]piperidineHCID 23676156Sodium t-butoxide

생성물 1

HCID 684830771-[4-(Phenylmethoxy)phenyl]-4-[4-(trifluoromethoxy)phenoxy]piperidine수율 98.4%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 23136663Tri-tert-butylphosphonium Tetraphenylborate촉매HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

4-[4-(Trifluoromethoxy)phenoxy]piperidine (2.61 g), benzyl 4-bromophenyl ether (2.63 g), palladium (II) acetate (0.67 mg), Tri-tert-butyl phosphonium tetraphenyl borate (1.57 mg), sodium tert-butoxide (1.06 g) and toluene (13 mL) were placed in a vessel and heated to reflux for 6 hr under Ar. The reaction mixture was then cooled to room temperature and water (100 mL) and ethyl acetate (100 mL) were added. The organic material was taken up in ethyl acetate. The organic layer was washed three times with water (100 mL×3). The organic layer was filtered to remove harz and then the organic layer was condensed under reduced pressure to afford 4.36 g (98.4% yield) of a pale yellow crystal target compound.

후처리

  1. temperatureheated
  2. temperatureto reflux for 6 hr under Ar
  3. washThe organic layer was washed three times with water (100 mL×3)
  4. filtrationThe organic layer was filtered
  5. customto remove harz
  6. customcondensed under reduced pressure

출처 및 근거

ORD 기록
ord-eda3b3c11fd94f64a01bdd352d557dd0
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552188B2

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