N-(2-Aminoethyl)-1,3-propanediamine → HCID 17944091, compound

HRID 1165911Notes

Reaction equation

HRID 1165911 reaction equation
C(NCC(O)=O)C1C=CC=CC=1.NCCNCCCN.[NH2:21][CH2:22][C:23]([NH:25][CH2:26][CH2:27][NH:28][CH2:29][CH2:30][CH2:31][NH:32][C:33](=[O:36])[CH2:34][NH2:35])=[O:24].C(NCC([N:48]([CH2:63][CH2:64][CH2:65][NH:66][C:67](=[O:77])[CH2:68][NH:69]CC1C=CC=CC=1)[CH2:49][CH2:50][NH:51][C:52](=[O:62])[CH2:53][NH:54]CC1C=CC=CC=1)=O)C1C=CC=CC=1>CN(C)C=O>[NH2:21][CH2:22][C:23]([NH:25][CH2:26][CH2:27][NH:28][CH2:29][CH2:30][CH2:31][NH:32][C:33](=[O:36])[CH2:34][NH2:35])=[O:24].[NH2:21][CH2:22][C:23]([NH:25][N:48]([CH2:63][CH2:64][CH2:65][NH:66][C:67](=[O:77])[CH2:68][NH2:69])[CH2:49][CH2:50][NH:51][C:52](=[O:62])[CH2:53][NH2:54])=[O:24]

Participants

7

Reactant 4

HCID 26091N-(2-Aminoethyl)-1,3-propanediamineHCID 869652-(Benzylamino)acetic acidHCID 53777645HCID 53777645, compoundHCID 54472393HCID 54472393, compound

Product 2

HCID 17944091HCID 17944091, compoundHCID 54472393HCID 54472393, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The p-nitrophenyl ester of N-benzylglycine and N-(2-aminoethyl)-1,3-propane diamine are reacted in the same proportions as in (A) above but in dimethyl formamide as the solvent to yield, after working up in a similar manner, N-(N-benzylglycyl)-N-[2-(benzylaminoacetamido)-ethyl]-3-(benzylaminoacetamido)-propylamine in 65% yield, δ(d6DMSO) 1.6 (m, 2H), 3.2 (m, 6H), 3.5 (d, 4H), 3.8 (d, 2H), 5.0 (s, 6H), 7.3 (s, 15H), 7.4 (m, 3H), 7.8 (m, 3H). Hydrogenation as in (A) above yields the title compound in 75% yield as an oil.

Workup

  1. customto yield

Sources & evidence

ORD record
ord-0997689eb01f4d44bb8af2fdd534cf82
Source dataset
uspto-grants-1990_03
Patent number
US04912118

Reaction notes

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