Hydrochloric Acid → 1-[(3,4-Dimethoxyphenyl)-2-propyl]amino-3-(1-naphthyloxy)propan-2-ol

HRID 374532Notes

Reaction equation

HRID 374532 reaction equation
[NH2:1][C@H:2]([CH3:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1.C[Si](C)(C)NC(=O)C.[C:23]1([O:33][CH2:34][CH:35]2[O:37][CH2:36]2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.Cl.[OH-].[Na+]>CS(C)=O>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([CH2:3][CH:2]([NH:1][CH2:36][CH:35]([OH:37])[CH2:34][O:33][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[CH3:14])[CH:9]=[CH:8][C:7]=1[O:10][CH3:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25989Acetamide, N-(trimethylsilyl)-HCID 915212-((1-Naphthalenyloxy)methyl)oxiraneHCID 117694083,4-Dma, (R)-

Product 1

HCID 545338521-[(3,4-Dimethoxyphenyl)-2-propyl]amino-3-(1-naphthyloxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 4.20 g of (R)-2-Amino-1-(3,4-dimethoxyphenyl)propane and 3.11 g of N-(trimethylsilyl)acetamide in 20 ml of dimethylsulfoxide is stirred at room temperature for 1 hour. A solution of 4.05 g of (1-naphthyl)glycidyl ether in 3 ml of dimethylsulfoxide is added to the above mixture and the resulting mixture is heated at 65° C. to 70° C. for 20 hours, cooled, poured into a mixture of ice and concentrated hydrochloric acid, stirred, basified with 10N sodium hydroxide and extracted with ethyl acetate. The ethyl acetate extract is washed with brine, dried, filtered and evaporated to yield 1-[(3,4-dimethoxyphenyl)-2-propyl]amino-3-(1- naphthyloxy)propan-2-ol.

Workup

  1. temperaturethe resulting mixture is heated at 65° C. to 70° C. for 20 hours
  2. temperaturecooled
  3. stirringstirred
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washis washed with brine
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-762f2c25e3704937938ec1b6355b3e56
Source dataset
uspto-grants-1996_01
Patent number
US05480908

Reaction notes

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