Potassium Carbonate → 1-(2-(6,11-Dihydrodibenzo[b,e]thiepin-11-ylidene)-1-ethyl)-4-piperidinecarboxylic acid ethyl ester hydrogen oxalate

HRID 612443노트

반응식

HRID 612443 반응식
Br[CH2:2][CH:3]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][S:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2.[C:19](=[O:22])([O-:21])[O-].[K+].[K+].[CH2:25]([O:27][C:28]([CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:29])[CH3:26]>CS(C)=O.C1C=CC=CC=1.[I-].[Na+]>[C:28]([OH:29])(=[O:27])[C:19]([OH:21])=[O:22].[CH2:25]([O:27][C:28]([CH:30]1[CH2:35][CH2:34][N:33]([CH2:2][CH:3]=[C:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][S:7][C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]2=3)[CH2:32][CH2:31]1)=[O:29])[CH3:26]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 5396280411-(2-Bromoethylidene)-6,11-dihydrodibenzo[b,e]thiepine

생성물 1

HCID 699489471-(2-(6,11-Dihydrodibenzo[b,e]thiepin-11-ylidene)-1-ethyl)-4-piperidinecarboxylic acid ethyl ester hydrogen oxalate수율 72%

시약·촉매·용매 3

HCID 5238Sodium Iodide촉매HCID 241Benzene용매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
100 °C

실험 절차

To a solution of 11-(2-bromoethylidene)-6,11-dihydrodibenzo[b,e]thiepine (4.76 g, 0.015 mol, prepared similarly as described in Coll. Czech. Chem. Comm. 52, 1566, 1987) in dimethylsulfoxide (90 ml), potassium carbonate (3.1 g, 0.0225 mol), 4-piperidinecarboxylic acid ethyl ester (2.36 g, 0.015 mol) and sodium iodide (50 mg) were added and the mixture was stirred at 100° C. for 4 h. The reaction mixture was diluted with benzene (100 ml), the solid was filtered off and the filtrate was washed with water (4×60 ml). The benzene solution was dried (MgSO4) and the solvent removed in vacuo. The oily residue (6.34 g) was dissolved in acetone and treated with an ethanolic solution of oxalic acid. The resulting precipitate was filtered off and washed with a hot mixture of ethanol and acetone, affording 5.2 g (72%) of 1-(2-(6,11-dihydrodibenzo[b,e]thiepin-11-ylidene)-1-ethyl)-4-piperidinecarboxylic acid ethyl ester hydrogen oxalate.

후처리

  1. filtrationthe solid was filtered off
  2. washthe filtrate was washed with water (4×60 ml)
  3. dry with materialThe benzene solution was dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. dissolutionThe oily residue (6.34 g) was dissolved in acetone
  6. additiontreated with an ethanolic solution of oxalic acid
  7. filtrationThe resulting precipitate was filtered off
  8. washwashed with a hot mixture of ethanol and acetone

출처 및 근거

ORD 기록
ord-a01a8f87d24b4cfcbd7c568aee95928f
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06004983

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