P-Anisidine → (R)-[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-methoxy-phenyl)-amine

HRID 1726232Notes

Reaction equation

HRID 1726232 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.O=[C:11]1[CH2:16][CH2:15][N:14]([C@H:17]([CH3:21])[CH2:18][C:19]#[N:20])[CH2:13][CH2:12]1>>[NH2:20][CH2:19][CH2:18][C@H:17]([N:14]1[CH2:15][CH2:16][CH:11]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:12][CH2:13]1)[CH3:21]

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 68972438(betaR)-beta-Methyl-4-oxo-1-piperidinepropanenitrile

Product 1

HCID 68970439(R)-[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-methoxy-phenyl)-amine

Procedure

Using general procedure A with p-anisidine (738 mg, 6.00 mmol) and (R)-3-(4-oxo-piperidin-1-yl)-butyronitrile (1.11 g, 6.67 mmol) followed by general procedure J gave [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-methoxy-phenyl)-amine as an orange oil (1.43 g, 86% over 2 steps).

Sources & evidence

ORD record
ord-b60305875f8e4c238d5689aebc75382f
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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