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 622734노트

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HRID 622734 반응식
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]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13370972HCID 13370972, 화합물HCID 22158922HCID 22158922, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 180Acetone용매HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 6228Dimethylformamide용매

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온도
105 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-8bfc1194e520441abdd59687f78d612b
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04772621

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