Dimethylformamide → Benzylamine

HRID 859231Notes

Reaction equation

HRID 859231 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[CH2:8]1[CH2:12]O[CH2:10][CH2:9]1.[CH3:13]N(C=O)C.[CH3:18]C(N(C)C)=O>C(Cl)(Cl)Cl.C(#N)C>[CH2:6]([NH2:3])[C:7]1[CH:13]=[CH:12][CH:8]=[CH:9][CH:10]=1.[CH:6]([N:3]([CH:8]([CH3:12])[CH3:9])[CH2:4][CH3:5])([CH3:7])[CH3:18]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31374Dimethylacetamide

Product 2

HCID 7504BenzylamineHCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

Step 1 The first step of Scheme 1 is accomplished by treating Compound i (Ref. U.S. Ser. No. 60/533,335 filed Dec. 29, 2003) with a benzyl amine, or a substituted benzyl amine, in the presence of a tertiary base such as triethylamine, or diisopropylethylamine, in an anhydrous solvents such as THF, DMF, DMA, acetonitrile or chloroform, at a temperature between about 20° C. to about 120° C., to give an ammonium salt, Compound ii.

Sources & evidence

ORD record
ord-770c0e153ac1441fa2ab05fe15351e71
Source dataset
uspto-grants-2006_12
Patent number
US07151176B2

Reaction notes

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