4-(Trifluoromethyl)aniline → [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-trifluoromethyl-phenyl)-amine

HRID 1726280Notes

Reaction equation

HRID 1726280 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.O=[C:13]1[CH2:18][CH2:17][N:16]([C@H:19]([CH3:23])[CH2:20][C:21]#[N:22])[CH2:15][CH2:14]1>>[NH2:22][CH2:21][CH2:20][C@H:19]([N:16]1[CH2:17][CH2:18][CH:13]([NH:7][C:6]2[CH:8]=[CH:9][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:4][CH:5]=2)[CH2:14][CH2:15]1)[CH3:23]

Participants

3

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 68972438(betaR)-beta-Methyl-4-oxo-1-piperidinepropanenitrile

Product 1

HCID 68970065[1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-trifluoromethyl-phenyl)-amine

Procedure

Using general procedure A with 4-(trifluoromethyl)aniline (0.19 mL, 1.51 mmol) and (R)-3-(4-oxo-piperidin-1-yl)-butyronitrile (302 mg, 1.82 mmol) followed by general procedure J afforded [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-trifluoromethyl-phenyl)-amine as a pale blue solid (232 mg, 49% over 2 steps).

Sources & evidence

ORD record
ord-ecbe790b614143a990c224836a4ed1ff
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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