Methylamine → N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)-N-methyl-m-dithiane-2-propylamine

HRID 616312

反応式

HRID 616312 の反応式
[C:1](O)(=O)[CH2:2][C:3]1[CH:12]=[CH:11][C:8]([O:9][CH3:10])=[C:5]([O:6][CH3:7])[CH:4]=1.C(OC(Cl)=O)C(C)C.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C:33]2([CH2:39][CH2:40][CH2:41][NH:42][CH3:43])[S:38][CH2:37][CH2:36][CH2:35][S:34]2)[CH:28]=[CH:29][C:30]=1[O:31][CH3:32].ClCCCC1(C2C=CC(OC)=C(OC)C=2)SCCCS1.CN>O1CCCC1.C(N(CC)CC)C>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:12]=[CH:11][C:8]=1[O:9][CH3:10])[CH2:2][CH2:1][N:42]([CH3:43])[CH2:41][CH2:40][CH2:39][C:33]1([C:27]2[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:25]([O:24][CH3:23])[CH:26]=2)[S:38][CH2:37][CH2:36][CH2:35][S:34]1

参加物

8

反応物 5

HCID 6329MethylamineHCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 62365Isobutyl chloroformateHCID 12462833HCID 12462833、化合物HCID 22758365HCID 22758365、化合物

生成物 1

HCID 9983099N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)-N-methyl-m-dithiane-2-propylamine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒

実験手順

1 g of homoveratric acid is dissolved in 15 ml of absolute tetrahydrofuran and treated with 0.15 g of triethylamine. 0.72 g of chloroformic acid isobutyl ester are then slowly added dropwise at 0°-5° C and the mixture is stirred for 1 hour at 5°-10° C. There is then added dropwise a solution of 1.63 g of 2-(3,4-dimethoxyphenyl)-N-methyl-m-dithiane-2-propylamine prepared in a manner analogous to that described in Example 15 from 2-(γ-chloropropyl)-2-(3,4-dimethoxyphenyl)-m-dithiane and methylamine! in 5 ml of tetrahydrofuran. The resulting mixture is left to stand at room temperature overnight. After evaporation of the solvent, the residue is partitioned between 1-M hydrochloric acid and ether. The organic extracts are washed with 5% sodium carbonate solution and water. After drying over magnesium sulphate, the solvent is removed by evaporation. The oily residue (1.5g) is dissolved in 15 ml of tetrahydofuran and added dropwise to a suspension of 0.15 g of lithium aluminium hydride under reflux and under argon. The mixture is boiled for 2 hours and then treated slowly with a concentrated sodium sulphate solution in water and then with 10 ml of methylene chloride. The mixture is filtered under suction and then concentrated. The residue is chromatographed on silica gel and there is obtained N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)-N-methyl-m-dithiane-2-propylamine in the form of a thick oil.

後処理

  1. customprepared in a manner analogous to
  2. waitThe resulting mixture is left
  3. waitto stand at room temperature overnight
  4. customAfter evaporation of the solvent
  5. customthe residue is partitioned between 1-M hydrochloric acid and ether
  6. washThe organic extracts are washed with 5% sodium carbonate solution and water
  7. dry with materialAfter drying over magnesium sulphate
  8. customthe solvent is removed by evaporation
  9. dissolutionThe oily residue (1.5g) is dissolved in 15 ml of tetrahydofuran
  10. additionadded dropwise to a suspension of 0.15 g of lithium aluminium hydride
  11. temperatureunder reflux and under argon
  12. waitThe mixture is boiled for 2 hours
  13. additiontreated slowly with a concentrated sodium sulphate solution in water
  14. filtrationThe mixture is filtered under suction
  15. concentrationconcentrated
  16. customThe residue is chromatographed on silica gel

出典と根拠

ORDレコード
ord-9eb88d8837d1488caae6bf43be450672
出典データセット
uspto-grants-1978_02
特許番号
US04073797

関連ノート

読み込み中…