Aniline → HCID 67183029, compound

HRID 1966479Notes

Reaction equation

HRID 1966479 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([N:18]2[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]2)[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:20][CH2:19]2)[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67183654HCID 67183654, compound

Product 1

HCID 67183029HCID 67183029, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(3-(benzylamino)-4-nitrophenyl)piperidine-4-carboxylic acid (0.2 g, 0.56 mmol) and aniline (0.052 mL, 0.56 mmol) in DMF (5 mL) was added diisopropylethylamine (0.198 mL, 1.12 mmol) under argon. The mixture cooled to 0° C., HATU (0.212 g, 0.56 mmol) was added at that temperature and then stirred at room temperature for 4 h. After completion of reaction (by TLC), H2O (5 mL) was added drop by drop. The resulting yellow precipitate was filtered, washed with 2 mL of water, dried (high vacuum, 14 h) to furnish 1-(3-(benzylamino)-4-nitrophenyl)-N-phenyl piperidine-4-carboxamide (0.21 g), 87% yield. 1H NMR (500 MHz, DMSO): δ 1.57 (m, 2H), 1.82 (m, 2H), 2.65 (m, 1H), 2.99 (m, 2H), 3.98 (m, 2H), 4.60 (d, J=5.7 Hz, 2H), 5.97 (d, J=2.5 Hz, 1H), 6.44 (dd, J=2.5 Hz, 1H), 7.03 (m, 1H), 7.29 (m, 3H) 7.37 (m, 2H), 7.43 (m, 2H), 7.60 (m, 2H), 7.92 (d, J=9.7 Hz, 1H), 8.84 (m, 1H), 9.9 (bs, 1H). HRMS (ESI) calculated for C25H27N4O3: 431.2078, Found: 431.2005.

Workup

  1. additionwas added drop by drop
  2. filtrationThe resulting yellow precipitate was filtered
  3. washwashed with 2 mL of water
  4. customdried (high vacuum, 14 h)

Sources & evidence

ORD record
ord-29db109cf9dc46c88874abbc1e96d444
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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