Water → HCID 12741431, compound

HRID 1164501Notes

Reaction equation

HRID 1164501 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)=[CH:5][CH:4]=1.[CH2:14]([NH:17][CH2:18][CH2:19][CH3:20])[CH2:15][CH3:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1.[Pt]=O.C(O)C>[CH2:14]([N:17]([CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10]1)[CH2:18][CH2:19][CH3:20])[CH2:15][CH3:16]

Participants

8

Reactant 4

HCID 962WaterHCID 8902DipropylamineHCID 777857-Methoxy-2-tetraloneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 12741431HCID 12741431, compoundYield 69.8%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 241BenzeneSolvent2×HCID 702EthanolSolvent

Procedure

7-Methoxy-2-tetralone (35.1 g, 0.20 mole) was dissolved in dry benzene (1000 ml) and put in a 2000 ml three neck-flask. To this solution was added dipropylamine (109 ml, 0.80 mole) and p-toluenesulfonic acid monohydrate (34 g, 0.2 mole). This mixture was refluxed under nitrogen with continuous water removal for 48 hr. The benzene was replaced by ethanol (600 ml, anhydrous) and the solution was hydrogenated in a 2 liter pressure bottle over platinum oxide (1.0 g) under 2 atmospheres of pressure at room temperature for 2.5 hr. The solution was filtered through cellulose powder and concentrated. Benzene was added to the filtrate. The organic solution was basified with 10% sodium hydroxide, washed with water and extracted with 5% hydrochloric acid. The aqueous solution was basified with 10% sodium hydroxide and extracted with diethyl ether. The organic extract was dried and evaporated to give a brown liquid (36.5 g) of N,N-dipropyl-7-methoxy-1,2,3,4-tetrahydro-2-naphthylamine. A sample was purified by chromatography through a column of silica gel using 2% methanol-chloroform mixture as eluant. The hydrochloride salt was prepared and crystallized from methanol and diethyl ether: mp 152-157° C., and Anal. Calcd for C17H28NOCl.1/2H2O:C, 66.53%;H, 9.45%;N, 4.56%; and Found:C, 66.39%;H, 9.40%;N, 4.39%.

Workup

  1. filtrationThe solution was filtered through cellulose powder
  2. concentrationconcentrated
  3. additionBenzene was added to the filtrate
  4. washwashed with water
  5. extractionextracted with 5% hydrochloric acid
  6. extractionextracted with diethyl ether
  7. extractionThe organic extract
  8. customwas dried
  9. customevaporated

Sources & evidence

ORD record
ord-a7a2bfa03d2242b7b840eb2a23ef3e9d
Source dataset
uspto-grants-1983_01
Patent number
US04370341

Reaction notes

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