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

HRID 247462

Reaction equation

HRID 247462 reaction equation
[C:1]1([C:7]([CH:9]=O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:11].[NH2:12][CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[CH:18][CH:19]=2)[CH2:14]1.[BH4-].[Na+].O>CO>[ClH:11].[CH3:24][O:23][C:17]1[CH:16]=[C:15]2[C:20]([CH2:21][CH2:22][CH:13]([NH:12][CH2:9][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[OH:8])[CH2:14]2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14090PhenylglyoxalHCID 4311764Sodium borohydride2×HCID 147509157-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine hydrochloride

Product 1

HCID 201608852-[(7-Methoxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-phenylethanol hydrochlorideYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
4 °C

Procedure

An amount of 3.53 g of phenylglyoxal is reacted under stirring at room temperature for 3 hours with 5 g of 2-amino-7-methoxy-1,2,3,4-tetrahydronaphthalene hydrochloride in 100 ml of methanol in the presence of 0.9 g of sodium borohydride. After cooling to 4° C., 4,3 g of sodium borohydride are added and the reacting mixture is left under stirring at room temperature for a night. After addition of 20 ml of water, the solution is stirred at room temperature for 15 minutes, then it is evaporated to dryness. The residue is dissolved in 300 ml of ethyl acetate and 60 ml of water; after filtration, the organic phase is separated, dried over magnesium sulfate, filtered and evaporated to dryness. The oil thus obtained is purified by flash-chromatography by using a mixture ethyl acetate/methanol 8/2 as eluant to obtain the 2-[(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-phenylethanol hydrochloride. Yield: 20% of the theoretical value.

Workup

  1. waitthe reacting mixture is left
  2. stirringthe solution is stirred at room temperature for 15 minutes
  3. customit is evaporated to dryness
  4. dissolutionThe residue is dissolved in 300 ml of ethyl acetate
  5. filtrationafter filtration
  6. customthe organic phase is separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe oil thus obtained
  11. customis purified by flash-chromatography

Sources & evidence

ORD record
ord-a395cc8371f745c7a98988b156bd69c4
Source dataset
uspto-grants-1987_11
Patent number
US04707497

Linked notes

Loading…