N-Phenylacrylamide → N1-Phenyl-3-(7-benzyl-3,7-diazabicyclo[3.3.1]non-3-yl)propanamide

HRID 1596450

Reaction equation

HRID 1596450 reaction equation
[C:1]1([NH:7][C:8](=[O:11])[CH:9]=[CH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:12]([N:19]1[CH2:26][CH:25]2[CH2:27][CH:21]([CH2:22][NH:23][CH2:24]2)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCO>[C:1]1([NH:7][C:8](=[O:11])[CH2:9][CH2:10][N:23]2[CH2:24][CH:25]3[CH2:27][CH:21]([CH2:20][N:19]([CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:26]3)[CH2:22]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 221792N-PhenylacrylamideHCID 130594823-Benzyl-3,7-diazabicyclo[3.3.1]nonane

Product 1

HCID 21701928N1-Phenyl-3-(7-benzyl-3,7-diazabicyclo[3.3.1]non-3-yl)propanamideYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N1-Phenylacrylamide (1.0 g; 6.8 mmol; from step (a) above) was added to a stirred solution of 3-benzyl-3,7-diazabicyclo[3.3.1]nonane (1.5 g; 6.8 mmol; see Example E above) in EtOH (7 mL). The reaction mixture was stirred for 10 h and concentrated to give the sub-title compound in a 97% yield.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-f0574f3b183b4cd1bb0361e693c30f5d
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Linked notes

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