Ammonia → HCID 20524093, compound

HRID 1702928Notes

Reaction equation

HRID 1702928 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][CH2:12][NH2:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1.C(N(CC)CC)C.N>CN(C)C=O.C(Cl)Cl>[C:1]([NH:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 769243-(2-Bromoethyl)indoleHCID 238993n-(3-Aminopropyl)benzamide

Product 1

HCID 20524093HCID 20524093, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 8 g N-benzoyl-1,3-diaminopropane, 6,7 g 3-(2-bromoethyl)indole and 5 ml anhydrous triethylamine in 15 ml anhydrous dimethylformamide is maintained for 72 hours in nitrogen atmosphere. A dilute ammonia solution and methylene chloride are then added to the reaction mixture and the organic phase is dried and evaporated. The residue is chromatographied on silicagel using as eluant methylene chloride+5% methanol+0.3% ammonia, to yield the title compound (M.pt. of the naphthalene-2-sulfonate 203°-204° with decomposition after crystallization from ethanol).

Workup

  1. customthe organic phase is dried
  2. customevaporated

Sources & evidence

ORD record
ord-54a091c66dbb4da29929d6f73f6cb17f
Source dataset
uspto-grants-1982_09
Patent number
US04350634

Reaction notes

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