p-Toluenesulfonic acid → HCID 20379960, compound

HRID 2420112Notes

Reaction equation

HRID 2420112 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]([OH:16])[CH2:12][N:13]([CH3:15])[CH3:14])=[CH:2]1.[C:17]1(C)[CH:22]=CC(S(O)(=O)=O)=C[CH:18]=1>CC(C)=O>[CH3:14][N:13]([CH2:12][CH:11]1[O:16][C:17]([CH3:22])([CH3:18])[C:2]2[NH:1][C:9]3[C:4]([C:3]=2[CH2:10]1)=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH3:15]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 20379979HCID 20379979, compound

Product 1

HCID 20379960HCID 20379960, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixtue of 1-(indol-3-yl)-3-(dimethylamino)propan-2-ol [9.5 g, 0.00435 mole, described by Z. G. Starostina et al., Khim.-Farm. Zh., 6, 14(1972) (Chem. Abstr., 78, 58185 r)] and p-toluenesulfonic acid (10 g, 0.0525 mole) in dry acetone (100 ml), is refluxed for 24 hours. The reaction mixture is evaporated and the residue is dissolved in water. The aqueous acidic solution is extracted with diethyl ether and the aqueous phase is basified with a saturated solution of sodium carbonate. The alkaline aqueous phase is extracted with diethyl ether and the organic extract is dried over magnesium sulfate, treated with charcoal and evaporated to give a residue of 3-[(dimethylamino)methyl]-1,3,4,9-tetrahydro-1,1-dimethylpyrano-[3,4-b]indole, a compound of formula II. The hydrochloride salt of the latter compound is crystallized from acetonitrite, mp 213°-215° C.

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in water
  3. extractionThe aqueous acidic solution is extracted with diethyl ether
  4. extractionThe alkaline aqueous phase is extracted with diethyl ether
  5. extractionthe organic extract
  6. dry with materialis dried over magnesium sulfate
  7. additiontreated with charcoal
  8. customevaporated

Sources & evidence

ORD record
ord-f3a16db6c26e4e628f512cc661eeeb94
Source dataset
uspto-grants-1978_08
Patent number
US04108998

Reaction notes

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