Water → HCID 20160833, 화합물

HRID 982000노트

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HRID 982000 반응식
[CH3:1][C:2]1[NH:3][C:4]([CH3:27])=[C:5]([C:21]([O:23][CH2:24][CH2:25]Br)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[ClH:28].[C:29]1([C:35]2([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[ClH:28].[CH3:1][C:2]1[NH:3][C:4]([CH3:27])=[C:5]([C:21]([O:23][CH2:24][CH2:25][N:38]2[CH2:39][CH2:40][C:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:36][CH2:37]2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 30475044,4-Diphenylpiperidine hydrochlorideHCID 22158922HCID 22158922, 화합물

생성물 1

HCID 20160833HCID 20160833, 화합물수율 41.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2.35 g of 3-methyl 5-(2-bromoethyl) (+)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate, 1.46 g of 4,4-diphenylpiperidine hydrochloride and 1.55 g of finely powdered potassium carbonate in 15 ml of anhydrous dimethylformamide are stirred for 6 h at 80° C. After the mixture has cooled, 100 ml of water are added and the mixture is then extracted with ether. The ether phase is washed twice with water, dried over sodium sulphate and then evaporated in vacuo. The residue is chromatographed over a silica gel column using a 95:5 chloroform/ethanol as the mobile phase. The chromatographically pure fractions are collected and evaporated. The residue is dissolved in ether and 2 ml of a saturated solution of hydrogen chloride in ether are added to the solution, crystallisation occurring. The product is filtered off under suction, washed with ether and dried. 1.4 g of the title compound of m.p. 155°-158° C. (decomp.) and [α]22D =+68.4° (c=1, methanol) are obtained.

후처리

  1. temperatureAfter the mixture has cooled
  2. extractionthe mixture is then extracted with ether
  3. washThe ether phase is washed twice with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo
  6. customThe residue is chromatographed over a silica gel column
  7. customThe chromatographically pure fractions are collected
  8. customevaporated
  9. dissolutionThe residue is dissolved in ether
  10. addition2 ml of a saturated solution of hydrogen chloride in ether are added to the solution, crystallisation
  11. filtrationThe product is filtered off under suction
  12. washwashed with ether
  13. customdried

출처 및 근거

ORD 기록
ord-bcbc0ce2b568426a9726a752de67ee40
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04994461

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