Triethylamine → HCID 178499858, compound

HRID 1609014Notes

Reaction equation

HRID 1609014 reaction equation
[ClH:1].[NH2:2][CH2:3][CH2:4][C:5]1[CH:16]=[CH:15][C:8]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1.Cl.[N+](C1C=CC([C:27]2[CH:35]=[C:34]([NH:36][C:37]([NH2:39])=[NH:38])[CH:33]=[CH:32][C:28]=2[C:29](O)=[O:30])=CC=1)([O-])=O.C(N(CC)CC)C>CN(C)C=O>[ClH:1].[NH:36]([C:34]1[CH:35]=[CH:27][C:28]([C:29]([NH:2][CH2:3][CH2:4][C:5]2[CH:16]=[CH:15][C:8]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=2)=[O:30])=[CH:32][CH:33]=1)[C:37]([NH2:39])=[NH:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20083569100369-83-3HCID 178479384HCID 178479384, compound

Product 1

HCID 178499858HCID 178499858, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 486 mg of methyl 4-(2-aminoethyl)hydrocinnamate hydrochloride, 672 mg of 4-nitrophenyl-4-guanidino-benzoate hydrochloride, 404 mg of triethylamine and 10 ml of dimethylformamide was stirred at room temperature under argon for 5 hours. The reaction mixture was then evaporated to dryness in vacuo, and the residue was chromatographed on 25 g of MCI gel. 520 mg of amorphous methyl p-[2-(p-guanidinobenzamido)ethyl]hydrocinnamate hydrochloride were obtained. IR bands (KBr) at 3339, 3187, 1727, 1678, 1644, 1579, 1500, 1289, 1107, 852 cm-1.

Workup

  1. customThe reaction mixture was then evaporated to dryness in vacuo
  2. customthe residue was chromatographed on 25 g of MCI gel

Sources & evidence

ORD record
ord-da562338b62349a5a5e39415274e9d9e
Source dataset
uspto-grants-1995_03
Patent number
US05399585

Reaction notes

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