Hydrochloric Acid → 2-[(7-Methoxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-phenylethanol hydrochloride

HRID 247463

反応式

HRID 247463 の反応式
[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:12][CH3:13])=[CH:7][CH:8]=2)[CH2:3]1.C(N(CC)CC)C.Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24].[ClH:31]>O1CCCC1.C(O)(C)C>[ClH:31].[CH3:13][O:12][C:6]1[CH:5]=[C:4]2[C:9]([CH2:10][CH2:11][CH:2]([NH:1][CH2:22][CH:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[OH:24])[CH2:3]2)=[CH:8][CH:7]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 116080152-Amino-7-methoxytetralin

生成物 1

HCID 201608852-[(7-Methoxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-phenylethanol hydrochloride収率 30%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 1.77 g of 2-amino-7-methoxy-1,2,3,4-tetrahydronaphthalene and 1.1 g of triethylamine in 25 ml of tetrahydrofurane, there is added slowly 1.94 g of bromoacetophenone in 50 ml of tetrahdryofurane. The reaction mixture is left under stirring at room temperature for 2 hours, then is filtered andevaporated. The residue thus obtained is dissolved in isopropyl alcohol and acidified with a solution of hydrogen chloride in isopropyl alcohol, then it is precipitated with an etheral solution, filtered and dried. To the solution of the residue in 70 ml of methanol, cooled to 4° C., there is added slowly 1.5 g of sodium borohydride. The reaction mixture is stirred at room temperature for an hour, poured into water and acidified with acetic acid. The solution is made alkaline with sodium bicarbonate and the organic phase is extracted with methylene chloride, dried and evaporated to dryness. The oil thus obtained is purified by flash-chromatography using a mixture ethyl acetate/methanol 8/2. After recrystallization from isopropyl alcohol, the 2-[(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-phenylethanol hydrochloride is obtained. Yield: 30% of the theoretical value.

後処理

  1. waitThe reaction mixture is left
  2. filtrationis filtered
  3. customThe residue thus obtained
  4. customit is precipitated with an etheral solution
  5. filtrationfiltered
  6. customdried
  7. temperatureTo the solution of the residue in 70 ml of methanol, cooled to 4° C.
  8. additionthere is added slowly 1.5 g of sodium borohydride
  9. stirringThe reaction mixture is stirred at room temperature for an hour
  10. additionpoured into water
  11. extractionthe organic phase is extracted with methylene chloride
  12. customdried
  13. customevaporated to dryness
  14. customThe oil thus obtained
  15. customis purified by flash-chromatography
  16. customAfter recrystallization from isopropyl alcohol

出典と根拠

ORDレコード
ord-725482082f92474bb1b6a8bd9cd08878
出典データセット
uspto-grants-1987_11
特許番号
US04707497

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