Benzylamine → HCID 70179213, compound

HRID 2229430Notes

Reaction equation

HRID 2229430 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][CH2:12][C:13]([OH:15])=O)[C:4]=2[N:3]1[CH2:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=1.Cl.CN(C)CCCN=C=NCC.[CH2:41]([NH2:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=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][CH2:12][C:13]([NH:48][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:15])[C:4]=2[N:3]1[CH2:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70178072HCID 70178072, compound

Product 1

HCID 70179213HCID 70179213, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3-[2-Oxo-3-(3,4,5-trimethoxybenzyl)-benzimidazolyl]propionic acid (1.77 mmol, 0.69 g) (example 14) in DMA (5 ml) is charged with 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide HCl (2.66 mmol, 0.51g). 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. (R1=(CH2)2—C(O)—NHR5, x=2. R5=benzyl, R2=3,4,5-trimethoxybenzyl, n=0).

Workup

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

Sources & evidence

ORD record
ord-3fa7757e4d73417ab09f797dc86d022f
Source dataset
uspto-grants-2002_07
Patent number
US06420410B1

Reaction notes

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