4-(Aminomethyl)benzonitrile → (Rs)-n-(4-cyano-benzyl)-2-methoxy-2-(4-pyrrolidin-1-yl-phenyl)-acetamide

HRID 1247287Notes

Reaction equation

HRID 1247287 reaction equation
[CH2:1]1[CH2:5][N:4]([C:6]2[CH:11]=[CH:10][C:9](C=O)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[NH2:14][CH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.CO.[O:26]1[CH2:31][CH2:30][O:29][CH2:28]C1>>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([CH2:15][NH:14][C:31](=[O:26])[CH:30]([O:29][CH3:28])[C:9]2[CH:8]=[CH:7][C:6]([N:4]3[CH2:3][CH2:2][CH2:1][CH2:5]3)=[CH:11][CH:10]=2)=[CH:17][CH:18]=1)#[N:21]

Participants

4

Reactant 3

HCID 826084-(Aminomethyl)benzonitrileHCID 1040374-(1-Pyrrolidinyl)benzaldehydeHCID 21966525Dioxane Methanol

Product 1

HCID 21905106(Rs)-n-(4-cyano-benzyl)-2-methoxy-2-(4-pyrrolidin-1-yl-phenyl)-acetamide

Procedure

4-(1-Pyrrolidino)benzaldehyde was reacted according to general procedure A using methanol/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-methoxy-2-(4-pyrrolidin-1-yl-phenyl)-acetamide. Off-white solid. MS 350.4 ([M+H]+)

Sources & evidence

ORD record
ord-32c66ff237be47e485c53e9f2b13a167
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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