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

HRID 1726275Notes

Reaction equation

HRID 1726275 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.O=[C:14]1[CH2:19][CH2:18][N:17]([C@H:20]([CH3:24])[CH2:21][C:22]#[N:23])[CH2:16][CH2:15]1>>[NH2:23][CH2:22][CH2:21][C@H:20]([N:17]1[CH2:18][CH2:19][CH:14]([NH:8][C:7]2[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=2)[CH2:15][CH2:16]1)[CH3:24]

Participants

3

Reactant 2

HCID 6008484-(Trifluoromethoxy)anilineHCID 68972438(betaR)-beta-Methyl-4-oxo-1-piperidinepropanenitrile

Product 1

HCID 68971645[1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-trifluoromethoxy-phenyl)-amine

Procedure

Using general procedure A with 4-(trifluoromethoxy)-aniline (0.21 mL, 1.55 mmol) and (R)-3-(4-oxo-piperidin-1-yl]-butyronitrile (310 mg, 1.87 mmol) followed by general procedure J afforded [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-trifluoromethoxy-phenyl)-amine as a white solid (277 mg, 55% over 2 steps).

Sources & evidence

ORD record
ord-eca9bde9de43448b9db0ef25b1d736c8
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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