1-Butanol → N,alpha-Bis(4-Fluorophenyl)-1-[2(2-naphthalenyloxy)ethyl]-4-piperidinemethanamine hydrochloride

HRID 1614633

반응식

HRID 1614633 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[C:23]1(OCCBr)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[ClH:45].[CH2:46]([OH:50])[CH2:47]CC>CO.C(OCC)C>[ClH:45].[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[CH:10]2[CH2:15][CH2:14][N:13]([CH2:47][CH2:46][O:50][C:25]3[CH:24]=[CH:23][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=3)[CH2:12][CH2:11]2)=[CH:6][CH:7]=1

참가 물질

8

반응물 6

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 110759061-(2-Bromoethoxy)naphthaleneHCID 19771957N,alpha-bis(4-fluorophenyl)-4-piperidinemethanamine

생성물 1

HCID 19772009N,alpha-Bis(4-Fluorophenyl)-1-[2(2-naphthalenyloxy)ethyl]-4-piperidinemethanamine hydrochloride수율 36.3%

시약·촉매·용매 1

HCID 21864698Diethyl ether methanol용매

실험 절차

A mixture of N,α-bis(4-fluorophenyl)-4-piperidinemethanamine (3.42 g, 0.0113 mol), 2-bromoethyl naphthyl ether (2.83 g, 0.0113 mol), and potassium carbonate (3.46 g, 0.025 mol) was heated at reflux 16 h in 350 mL of 1-butanol containing sodium iodide (0.2 g). The reaction was concentrated to dryness, and the residue partitioned between chloroform and water. The chloroform layer was extracted with 5% sodium hydroxide. The organic layer was dried (Na2SO4) and filtered. The chloroform was removed by rotary evaporator to give a brown residue. This material was subjected to flash chromatography on silica gel. Elution was accomplished using methylene chloride, 1% methanol-methylene chloride, and 2% methanol-methylene chloride. Fractions of similar purity were combined and solvents removed. A brown residue was obtained and converted to the HCl salt in methanol-diethyl ether and placed in the freezer. A white solid was isolated and dried 16 h at 78° C. This process provided 2.24 g (36.3%) of white crystalline product mp 226°-230° C. (dec.).

후처리

  1. temperaturewas heated
  2. concentrationThe reaction was concentrated to dryness
  3. customthe residue partitioned between chloroform and water
  4. extractionThe chloroform layer was extracted with 5% sodium hydroxide
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customThe chloroform was removed by rotary evaporator
  8. customto give a brown residue
  9. washElution
  10. customsolvents removed
  11. customA brown residue was obtained
  12. customA white solid was isolated
  13. customdried 16 h at 78° C

출처 및 근거

ORD 기록
ord-2dae01b11616487984150efc5dfe29fc
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05198449

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