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

HRID 233389ノート

反応式

HRID 233389 の反応式
[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]

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 19961108HCID 19961108、化合物

生成物 1

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

実験手順

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 2 L 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).

後処理

  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

出典と根拠

ORDレコード
ord-736b99a180da46a8a24f63219659c8fa
出典データセット
uspto-grants-1997_01
特許番号
US05591884

反応ノート

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