Benzoyl chloride → HCID 20524090, compound

HRID 1702921Notes

Reaction equation

HRID 1702921 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][CH2:20][CH2:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25][NH2:26])=[CH:11]1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.N1C=CC=CC=1>[C:1]([NH:26][CH2:25][CH2:24][CH2:23][N:22]([CH2:21][CH2:20][CH2:19][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:10][CH:11]=1)[CH3:27])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 20524091HCID 20524091, compound

Product 1

HCID 20524090HCID 20524090, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.1 g benzoyl chloride in 15 ml anhydrous methylene chloride is added dropwise with stirring for 25 minutes between 0° and 10° to a solution of 14.5 g N-[3-(3-indolyl)propyl]-N-methyl-1,3-diaminopropane in 150 ml anhydrous pyridine and the reddish clear solution is stirred for 2 hours at 0°. The reaction mixture is divided between a 2 N sodium carbonate solution and methylene chloride, and the organic phase is washed, dried and evaporated. Chromatographic purification of the resinous product on aluminium oxide using methylene chloride with 0.1 to 0.3% of methanol yields the title compound. The naphthalene-2-sulfonate-dihydrate, obtained by conventional methods, melts at 73°-74° after crystallization from methanol/water/ethyl acetate (1:1:1).

Workup

  1. washthe organic phase is washed
  2. customdried
  3. customevaporated
  4. customChromatographic purification of the resinous product on aluminium oxide

Sources & evidence

ORD record
ord-e17b390c071343cf84678b4decf01db1
Source dataset
uspto-grants-1982_09
Patent number
US04350634

Reaction notes

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