Water → 1-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-(4-piperidinopiperid-1-yl)propyl]-piperidine dihydrochloride hemihydrate

HRID 50059

반응식

HRID 50059 반응식
[N:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:13].[C:14]([N:22]1[CH2:27][CH2:26][CH2:25][C:24]([C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[C:46]([Cl:51])[CH:45]=2)([CH2:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][CH:34](C(N3CCCC3)=O)[CH2:33][CH2:32]2)[CH2:23]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C(#N)C.CCOC(C)=O>[OH2:21].[ClH:50].[ClH:13].[C:14]([N:22]1[CH2:27][CH2:26][CH2:25][C:24]([C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[C:46]([Cl:51])[CH:45]=2)([CH2:28][CH2:29][CH2:30][N:10]2[CH2:11][CH2:12][CH:7]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:8][CH2:9]2)[CH2:23]1)(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1.[C:14]([N:22]1[CH2:27][CH2:26][CH2:25][C:24]([CH2:28][CH2:29][CH2:30][N:31]2[CH2:32][CH2:33][CH:34]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:35][CH2:36]2)([C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[C:46]([Cl:51])[CH:45]=2)[CH2:23]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[ClH:50].[ClH:50]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 786071,4'-BipiperidineHCID 227417141-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-[4-(pyrrolidin-1-ylcarbonyl)piperid-1-yl]propyl]piperidine hydrochloride

생성물 1

HCID 1317216521-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-(4-piperidinopiperid-1-yl)propyl]-piperidine dihydrochloride hemihydrate

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 21891449acetonitrile N,N-dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 0.55 g of 4-piperidinopiperidine, 1.3 g of the compound obtained in step B of EXAMPLE 1 and 1.14 g of K2CO3 in 10 ml of a DMF/acetonitrile mixture (50/50; v/v) is heated at 100° C. for 3 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 (98/2; v/v) as the eluent. The product obtained is dissolved in AcOEt, a stream of HCl gas is bubbled into the solution until the pH is 1, and ether is added until precipitation occurs. This gives 0.53 g of the expected product after filtration and drying, m.p.=265° C. (dec.).

후처리

  1. extractionextracted with AcOEt
  2. washthe organic phase is washed twice 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 H
  6. customThe product obtained
  7. customa stream of HCl gas is bubbled into the solution until the pH is 1, and ether
  8. additionis added until precipitation
  9. filtrationThis gives 0.53 g of the expected product after filtration
  10. customdrying

출처 및 근거

ORD 기록
ord-f5b4b110951240c1b5c5e985d48e12ea
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710042B2

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