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

HRID 247463

Reaction equation

HRID 247463 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-725482082f92474bb1b6a8bd9cd08878
Source dataset
uspto-grants-1987_11
Patent number
US04707497

Linked notes

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