4-(Aminomethyl)benzonitrile → (RS)-N-(4-cyano-benzyl)-2-(2-fluoro-4-methoxy-phenyl)-2-propoxy-acetamide

HRID 1247306Notes

Reaction equation

HRID 1247306 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[NH2:12][CH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.[CH2:22](O)[CH2:23][CH3:24].[O:26]1CCOC[CH2:27]1>>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([CH2:13][NH:12][C:27](=[O:26])[CH:4]([C:3]2[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:2]=2[F:1])[O:5][CH2:22][CH2:23][CH3:24])=[CH:15][CH:16]=1)#[N:19]

Participants

4

Reactant 3

HCID 826084-(Aminomethyl)benzonitrileHCID 27348732-Fluoro-4-methoxybenzaldehydeHCID 67832237n-Propanol dioxane

Product 1

HCID 21905254(RS)-N-(4-cyano-benzyl)-2-(2-fluoro-4-methoxy-phenyl)-2-propoxy-acetamide

Procedure

2-Fluoro-4-methoxybenzaldehyde was reacted according to general procedure A using n-propanol/dioxane as a solvent. The product of this reaction was subsequently coupled with 4-aminomethyl benzonitrile according to general procedure B to give (RS)-N-(4-cyano-benzyl)-2-(2-fluoro-4-methoxy-phenyl)-2-propoxy-acetamide. Light yellow oil. MS 357.2 ([M+H]+)

Sources & evidence

ORD record
ord-ba6269c2c4a84ada91df67086a928b33
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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