N-(3-fluoro-5-methyl-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine → (2-amino-3-fluoro-5-methylphenyl)[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amine

HRID 447793Notes

Reaction equation

[F:1][C:2]1[C:3]([N+:22]([O-])=O)=[C:4]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)[CH:5]=[C:6]([CH3:8])[CH:7]=1>[Pd].C(OCC)(=O)C>[NH2:22][C:3]1[C:2]([F:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of N-(3-fluoro-5-methyl-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (10 g), ethyl acetate (200 ml) and 10% Pd/C (1 g), was stirred at about 30° C. under hydrogen pressure for 9 hours. The catalyst was filtered and the filtrate concentrated. The residue was stirred with ethyl acetate (20 ml) and hexane (40 ml) for 1 hour at room temperature then filtered and the solid dried at 50° C. to give the title compound as a solid (6.3 g).

Workup

filtrationThe catalyst was filtered
concentrationthe filtrate concentrated
stirringThe residue was stirred with ethyl acetate (20 ml) and hexane (40 ml) for 1 hour at room temperature
filtrationthen filtered
customthe solid dried at 50° C.

Sources & evidence

ORD record: ord-39f665e56b584e63a5d66c69a9918cf0
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481566B2

Reaction notes

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