Ethyl orthoformate → 1-benzyl-4,5-dihydro-1H-imidazole

HRID 2377784Notes

Reaction equation

HRID 2377784 reaction equation
NCCC[N:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]1=O.C(NCCN)C1C=CC=CC=1.C(OC(OCC)OCC)C>>[CH2:10]([N:7]1[CH2:8][CH2:9][N:5]=[CH:6]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 31214Ethyl orthoformateHCID 77801N-BenzylethylenediamineHCID 69224605HCID 69224605, compound

Product 1

HCID 108774221-benzyl-4,5-dihydro-1H-imidazole

Procedure

As shown in FIG. 9B (Scheme 4), the synthesis of 1-(3-aminopropyl)-3-benzylimidazolidin-2-one (35) will be performed by treating the starting material N1-benzylethane-1,2-diamine with diethoxymethoxyethane to form 1-benzyl-4,5-dihydro-1H-imidazole. The imidazole intermediate will be treated with BuLi (forming a lithiate) followed by quenching with water to form the final intermediate 1-benzylimidazolidin-2-one. Treating the imidazolidinone with NaH followed by Br—(CH2)3—N(SiMe3)2 under reducing conditions will afford the intermediate 35.

Sources & evidence

ORD record
ord-79d5c8a412904410b706e10077374923
Source dataset
uspto-grants-2008_12
Patent number
US07470703B1

Reaction notes

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