Water → 5-[2-(4-Anilinopiperid-1-yl)ethyl]-3-[3,5-bis(trifluoromethyl)benzyl]-5-(3,4-dichlorophenyl)-tetrahydro-2H-1,3-oxazin-2-one dihydrochloride monohydrate

HRID 849339

반응식

HRID 849339 반응식
[NH:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:14][C:15]([F:50])([F:49])[C:16]1[CH:17]=[C:18]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:19][N:20]1[CH2:25][C:24]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=2)([CH2:26][CH2:27]OS(C)(=O)=O)[CH2:23][O:22][C:21]1=[O:41].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.CCOCC>[OH2:22].[ClH:39].[ClH:39].[NH:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:27][CH2:26][C:24]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=3)[CH2:23][O:22][C:21](=[O:41])[N:20]([CH2:19][C:18]3[CH:17]=[C:16]([C:15]([F:49])([F:50])[F:14])[CH:44]=[C:43]([C:45]([F:47])([F:46])[F:48])[CH:42]=3)[CH2:25]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 899824-AnilinopiperidineHCID 158866773-[3,5-Bis(trifluoromethyl)benzyl]-5-(3,4-dichlorophenyl)-5-[2-(methanesulfonyloxy)ethyl]tetrahydro-2H-1,3-oxazin-2-one

생성물 1

HCID 212004765-[2-(4-Anilinopiperid-1-yl)ethyl]-3-[3,5-bis(trifluoromethyl)benzyl]-5-(3,4-dichlorophenyl)-tetrahydro-2H-1,3-oxazin-2-one dihydrochloride monohydrate수율 9.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 0.3 g of 4-anilinopiperidine, 0. 8 g of the compound obtained in step C of EXAMPLE 4 and 0.69 g of potassium carbonate in 5 ml of acetonitrile is heated at 50-60° C. for 5 hours. The reaction mixture is poured into water and extracted with AcOEt, the organic phase is washed twice with water and with saturated NaCl solution and dried over Mgso4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H using DCM and then a DCM/MeOH mixture (96/4; v/v) as the eluent. The product obtained is taken up with a saturated solution of gaseous HC1 in ether and the precipitate formed is wrung to give 0.12 g of the expected product. M.p.=158° C.

후처리

  1. extractionextracted with AcOEt
  2. washthe organic phase is washed twice with water and with saturated NaCl solution
  3. customdried over Mgso4
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica H
  6. customThe product obtained
  7. customthe precipitate formed

출처 및 근거

ORD 기록
ord-f58aebc6ec584b219b427e6d0ad41442
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06011154

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