Benzylamine → HCID 70179520, compound

HRID 2229425Notes

Reaction equation

HRID 2229425 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][C:12]([OH:14])=O)[C:4]=2[N:3]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.CN(C)CCCN=C=NCC.[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CC(N(C)C)=O>[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][C:12]([NH:41][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:14])[C:4]=2[N:3]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70179137HCID 70179137, compound

Product 1

HCID 70179520HCID 70179520, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-(2-oxo-3-benzylbenzimidazolyl)acetic acid (1.77 mmol, 0.5 g) (example 2) in DMA (5 ml) is charged with 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide HCl (2.66 mmol, 0.51 g). Benzylamine (2.48 mmol, 0.27 ml) is added to the suspension, and the mixture is stirred at room temperature for 17 hours. The solution is added dropwise into ice (50 g) and the colorless precipitate is filtered off and dried in vacuo. Recrystallisation from ethyl acetate yields the title product (47%) (R1=CH2—C(O)—NHR5, R5=benzyl, R2=benzyl, n=0).

Workup

  1. filtrationthe colorless precipitate is filtered off
  2. customdried in vacuo
  3. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-b5acb280e8374b72a8c4eaa0baeb33ff
Source dataset
uspto-grants-2002_07
Patent number
US06420410B1

Reaction notes

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