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

HRID 612443ノート

反応式

HRID 612443 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 5238Sodium Iodide触媒HCID 241Benzene溶媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a01a8f87d24b4cfcbd7c568aee95928f
出典データセット
uspto-grants-1999_12
特許番号
US06004983

反応ノート

読み込み中…