Hydrochloric Acid → 5,6-Bis(acetoxy)-1-aminomethyl-3-phenyl-3,4-dihydronaphthalene hydrochloride

HRID 54126노트

반응식

HRID 54126 반응식
[ClH:1].[NH2:2][CH2:3][C:4]1[C:13]2[C:8](=[C:9]([OH:15])[C:10]([OH:14])=[CH:11][CH:12]=2)[CH2:7][CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:5]=1.Cl.C([O:25][CH2:26][CH3:27])C.[C:28](OC(=O)C)(=[O:30])[CH3:29]>>[ClH:1].[C:28]([O:15][C:9]1[C:10]([O:14][C:26](=[O:25])[CH3:27])=[CH:11][CH:12]=[C:13]2[C:8]=1[CH2:7][CH:6]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH:5]=[C:4]2[CH2:3][NH2:2])(=[O:30])[CH3:29]

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 19961108HCID 19961108, 화합물

생성물 1

HCID 199610845,6-Bis(acetoxy)-1-aminomethyl-3-phenyl-3,4-dihydronaphthalene hydrochloride수율 29%

실험 절차

A suspension of 7.6 g (25 mmol) of 1-aminomethyl-5,6-dihydroxy-3-phenyl-3,4-dihydronaphthalene hydrochloride (Example 2B) in 400 mL of acetic anhydride saturated with anhydrous hydrogen chloride was stirred at ambient temperature for 48 h. Approximately 2L of diethyl ether was added and a solid was collected by filtration and washed with diethyl ether. Crystallization of the crude material (6.7 g) was achieved by dissolving the powder in 400 mL of hot ethanol, adding 100 mL of water, filtering the solution hot and allowing it to cool. The white crystals which formed were filtered and dried to give 2.8 g (29% yield) of 5,6-bis(acetoxy)-1-aminomethyl-3-phenyl-3,4-dihydronaphthalene hydrochloride, m.p. 207°-208° C. 1H NMR (d6 -DMSO) δ: 2.28 (s, 6H), 2.62 (dd, 1H), 2.95 (dd, 1H), 3.7-3.8 (m, 1H), 3.97 (s, 2H), 6.25 (d, 1H), 7.19 (d, 1H), 7.2-7.4 (m, 6H), 8.41 (br s, 3H).

후처리

  1. filtrationa solid was collected by filtration
  2. washwashed with diethyl ether
  3. customCrystallization of the crude material (6.7 g)
  4. dissolutionby dissolving the powder in 400 mL of hot ethanol
  5. additionadding 100 mL of water
  6. filtrationfiltering the solution hot
  7. temperatureto cool
  8. customThe white crystals which formed
  9. filtrationwere filtered
  10. customdried

출처 및 근거

ORD 기록
ord-ef15df8ead284497a5565d7dc1ccd858
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05621133

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