Hydrochloric Acid → methyl N-(3,3-diphenylpropyl)-N-hydroxy-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

HRID 1073363ノート

反応式

HRID 1073363 の反応式
C(N(CC)CC)C.[OH:8][NH:9][CH2:10][CH2:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:25][C:26]1[NH:27][C:28]([CH3:51])=[C:29]([C:45]([O:47][CH2:48][CH2:49]Br)=[O:46])[CH:30]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([N+:42]([O-:44])=[O:43])[CH:37]=2)[C:31]=1[C:32]([O:34][CH3:35])=[O:33].Cl>CN(C)C=O.CC(C)=O.C(OCC)C.O>[CH3:25][C:26]1[NH:27][C:28]([CH3:51])=[C:29]([C:45]([O:47][CH2:48][CH2:49][N:9]([CH2:10][CH2:11][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[OH:8])=[O:46])[CH:30]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([N+:42]([O-:44])=[O:43])[CH:37]=2)[C:31]=1[C:32]([O:34][CH3:35])=[O:33]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13370972HCID 13370972、化合物HCID 22158922HCID 22158922、化合物

生成物 1

HCID 86741862methyl N-(3,3-diphenylpropyl)-N-hydroxy-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

試薬・触媒・溶媒 4

HCID 180Acetone溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
105 °C

実験手順

3 ml of triethylamine were added to a solution of 2.40 g of N-hydroxy-3,3-diphenylpropylamine in 17 ml of dimethylformamide. 4.39 g of methyl 2-bromoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate were added to the mixture. The mixture was then maintained in a nitrogen atmosphere and heated for 160 minutes at 105° C. After cooling, the mixture was poured into water and extracted with a diethyl ether: ethyl acetate mixture. The organic layer was washed many times with water and then dried. The solvent was evaporated off in vacuo. The oily residue obtained was purified first by chromatography on a silica gel column with ethyl acetate gradient in toluene and then on a silica gel column containing ammonia at 5.5% by weight with about 6N methanolic ammonia gradient in chloroform. The solid thus obtained was dissolved in a 2:1 by volume acetone: diethyl ether mixture and hydrogen chloride in diethyl ether was added. The hydrochloride hemihydrate of the title compound was filtered off, washed with isopropanol and dried at 100° C. and 0.5 mmHg for 1 hour. Yield 1.51 g, m.p. 100°-105° C.

後処理

  1. temperatureThe mixture was then maintained in a nitrogen atmosphere
  2. temperatureAfter cooling
  3. extractionextracted with a diethyl ether
  4. washThe organic layer was washed many times with water
  5. customdried
  6. customThe solvent was evaporated off in vacuo
  7. customThe oily residue obtained
  8. customwas purified first by chromatography on a silica gel column with ethyl acetate gradient in toluene
  9. additionon a silica gel column containing ammonia at 5.5% by weight with about 6N methanolic ammonia gradient in chloroform
  10. customThe solid thus obtained
  11. filtrationThe hydrochloride hemihydrate of the title compound was filtered off
  12. washwashed with isopropanol
  13. customdried at 100° C.

出典と根拠

ORDレコード
ord-3c3ad699b73147c9b08fbac2f501bb1f
出典データセット
uspto-grants-1990_11
特許番号
US04968832

反応ノート

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