Hydrochloric Acid → 3-[3-[4-(Acryloyl-N-methylamino)-4-phenylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine hydrochloride

HRID 377802노트

반응식

HRID 377802 반응식
Cl.[C:2]([N:6]([C:8]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[CH3:7])(=[O:5])[CH:3]=[CH2:4].[C:20]([N:28]1[CH2:33][CH2:32][CH2:31][C:30]([C:42]2[CH:47]=[CH:46][C:45]([Cl:48])=[C:44]([Cl:49])[CH:43]=2)([CH2:34][CH2:35][CH2:36]OS(C)(=O)=O)[CH2:29]1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C(Cl)Cl.O>[ClH:48].[C:2]([N:6]([C:8]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:10][N:11]([CH2:36][CH2:35][CH2:34][C:30]2([C:42]3[CH:47]=[CH:46][C:45]([Cl:48])=[C:44]([Cl:49])[CH:43]=3)[CH2:31][CH2:32][CH2:33][N:28]([C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:29]2)[CH2:12][CH2:13]1)[CH3:7])(=[O:5])[CH:3]=[CH2:4]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 118127101-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-(methanesulfonyloxy)propyl]piperidineHCID 227417164-(acryloyl-N-methylamino)-4-phenylpiperidine hydrochloride

생성물 1

HCID 227417863-[3-[4-(Acryloyl-N-methylamino)-4-phenylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine hydrochloride수율 63.8%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

A mixture of 0.27 g of 4-(acryloyl-N-methylamino)-4-phenylpiperidine hydrochloride, 0.45 g of the compound obtained in step B of EXAMPLE 1 and 0.3 g of K2CO3 in 3 ml of DMF is heated at 80° C. for 2 hours. The reaction mixture is poured into water and extracted with AcOEt, the organic phase is washed 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 using a gradient of a DCM/MeOH mixture (99/1; v/v to 95/5; v/v) as the eluent. The product obtained is dissolved in DCM and acidified by the addition of ethereal hydrogen chloride and the precipitate formed is filtered off to give 0.2 g of the expected product, m.p.=128° C.

후처리

  1. extractionextracted with AcOEt
  2. washthe organic phase is washed with water and with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica using a gradient of a DCM/MeOH mixture (99/1; v/v to 95/5; v/v) as the eluent
  6. customThe product obtained
  7. customthe precipitate formed
  8. filtrationis filtered off

출처 및 근거

ORD 기록
ord-b5204d6b1b394344972935e599743081
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06028082

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