Thionyl Chloride → HCID 18971629, compound

HRID 2395267Notes

Reaction equation

HRID 2395267 reaction equation
S(Cl)([Cl:3])=O.[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:14]([OH:16])=O.[CH2:17]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[ClH:3].[CH2:17]([N:24]1[CH2:29][CH2:28][N:27]([C:14]([C:6]2[NH:5][C:13]3[C:8]([CH:7]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)=[O:16])[CH2:26][CH2:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 72899Indole-2-carboxylic acidHCID 759941-Benzylpiperazine

Product 1

HCID 18971629HCID 18971629, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (1.62 ml, 22.3 mmol) was added to a solution of indole-2-carboxylic acid (3.0 g, 18.6 mmol) in toluene (40 ml), the mixture heated at reflux for 3 h and then cooled to room temperature. 1-Benzylpiperazine (3.7 ml, 20.4 mmol) was added and the resultant precipitate collected by filtration, washed with toluene, and dried in vacuo to give 2-(4-benzylpiperazin-1-yl) carbonyl indole hydrochloride (6.5 g, 98%). M.p. >210° C. (dec).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 h
  3. filtrationthe resultant precipitate collected by filtration
  4. washwashed with toluene
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a3faa32caba148bea79a0d927cc91de5
Source dataset
uspto-grants-1998_09
Patent number
US05814644

Reaction notes

Loading…