Sodium hydride → HCID 69224605, compound

HRID 2377785Notes

Reaction equation

HRID 2377785 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][N:20]([Si](C)(C)C)[Si](C)(C)C>>[NH2:20][CH2:19][CH2:18][CH2:17][N:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]1=[O:13]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 2314031-Benzylimidazolidin-2-oneHCID 11044237N,N-bis(trimethylsilyl)-3-bromo-1-propylamine

Product 1

HCID 69224605HCID 69224605, compound

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-1f5ff1878128401da119ad9b0e22c4f6
Source dataset
uspto-grants-2008_12
Patent number
US07470703B1

Reaction notes

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