p-Toluenesulfonic acid → HCID 14685742, compound

HRID 1088800Notes

Reaction equation

HRID 1088800 reaction equation
O=[C:2]1[C:11]2[C:6](=[C:7]([CH2:12][OH:13])[CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[CH2:4][CH2:3]1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH:16]1([NH:19][CH:2]2[C:11]3[C:6](=[C:7]([CH2:12][OH:13])[CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:14][CH3:15])[CH2:4][CH2:3]2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 69828CyclopropylamineHCID 14685740HCID 14685740, compound

Product 1

HCID 14685742HCID 14685742, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-oxo-1-ethyl-8-hydroxymethyl-1,2,3,4-tetrahydroquinoline (3.80 g) in methanol (40 ml), molecular sieve 3A (4 g), cyclopropylamine (11.42 g) and p-toluenesulfonic acid (catalytic amount) were added and the mixture was stirred for 8 hours at 65° C. After ice-cooling the reaction mixture, molecular sieve 3A was filtered off, then sodium borohydride (1.05 g) was added thereto, and the mixture was stirred for 1 hour at room temperature. A small amount of water was added to the reaction mixture, and methanol was distilled off. The residue was extracted with dichloromethane and dried over anhydrous magnesium sulfate. The solvent was distilled off and the resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (3:1)]to give 4-cyclopropylamino-8-hydroxymethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (3.69 g).

Workup

  1. filtrationwas filtered off
  2. additionsodium borohydride (1.05 g) was added
  3. stirringthe mixture was stirred for 1 hour at room temperature
  4. additionA small amount of water was added to the reaction mixture, and methanol
  5. distillationwas distilled off
  6. extractionThe residue was extracted with dichloromethane
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe resulting residue was purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-f96a9f0020bc40f8a069c5213353cebc
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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