Sulfuric Acid → HCID 15390685, compound

HRID 1377489Notes

Reaction equation

HRID 1377489 reaction equation
[C:1]([O:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=1)(=O)[CH3:2].[OH:20][CH2:21]CCO.S(=O)(=O)(O)O>O>[C:14]1([N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]([O:4][CH2:1][CH2:2][CH2:21][OH:20])=[CH:6]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 104421,3-PropanediolHCID 22012240HCID 22012240, compound

Product 1

HCID 15390685HCID 15390685, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-acetyloxy-1-phenylindole (24 g), 1,3-dihydroxypropane (240 ml), and conc. sulfuric acid (10 ml) was heated to 80° C. for 2 h. Water was added followed by extraction with ether. The ether phase was dried over magnesium sulfate followed by removal of solvent in vacuo giving 3-(1-phenyl-3-indolyloxy)-1-propanol, sufficiently pure for use in the next step. The title compound was obtained by the method described in EXAMPLE 2 using spiro[isobenzofuran-1(3H),4'-piperidine] and crystallized as the oxalate salt from acetone by addition of oxalic acid. Yield: 2 g, mp: 151°-54° C.

Workup

  1. extractionfollowed by extraction with ether
  2. dry with materialThe ether phase was dried over magnesium sulfate
  3. customfollowed by removal of solvent in vacuo

Sources & evidence

ORD record
ord-a5e9fb4f8bb14a75922094d4aef9c405
Source dataset
uspto-grants-1997_09
Patent number
US05665725

Reaction notes

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