Hydrochloric Acid → HCID 21524019, compound

HRID 917895Notes

Reaction equation

HRID 917895 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([N:14]([CH2:39][CH3:40])[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[C:25]2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:20][CH:19]=1)[CH3:13].C(O)(C)C.[ClH:45]>C(Cl)(Cl)Cl.O>[ClH:45].[CH2:39]([N:14]([CH2:12][CH3:13])[CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[C:25]2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:22][CH:23]=1)[CH3:40]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 21524022HCID 21524022, compound

Product 1

HCID 21524019HCID 21524019, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Following a procedure similar to that of Example 1E but using 28.53 g. of 1-(4-hydroxyphenyl)-2-phenylindole, 300 ml. of chlorobenzene, 5.45 g. of sodium methoxide in 68 ml. dry methyl alcohol, and 15 g. of N-(2-chloroethyl)diethylamine there was obtained 35 g. of crude product, 32 g. of which was converted to 30.1 g. of 1-{4-[2-(diethylamino)ethoxy]phenyl}-2-phenylindole p-toluenesulfonate; m.p. 123°-124°C. (isopropyl alcohol). A solution of the free base in chloroform was shaken with a slight excess of concentrated hydrochloric acid in water, the layers were separated, dried and concentrated. The residue was dissolved in isopropyl alcohol, concentrated, and diluted with ethyl acetate. The resulting solids were filtered to give 1-{4-[2-(diethylamino)ethoxy]phenyl}-2-phenylindole hydrochloride; m.p. 154°-155°C.

Workup

  1. customthe layers were separated
  2. customdried
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in isopropyl alcohol
  5. concentrationconcentrated
  6. additiondiluted with ethyl acetate
  7. filtrationThe resulting solids were filtered

Sources & evidence

ORD record
ord-e97f3ab9a1fc4419b12935f1efa4cbc5
Source dataset
uspto-grants-1976_07
Patent number
US03968121

Reaction notes

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