Benzylamine → HCID 67389904, compound

HRID 1966480Notes

Reaction equation

HRID 1966480 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.[CH2:27]([NH2:34])[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>[CH2:27]([NH:34][C:24]([CH:21]1[CH2:20][CH2:19][N:18]([C:11]2[CH:12]=[CH:13][C:14]([N+:15]([O-:17])=[O:16])=[C:9]([NH:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)[CH2:23][CH2:22]1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 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 67389904HCID 67389904, compoundYield 84.4%

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 benzylamine (0.06 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 N-benzyl-1-(3-(benzylamino)-4-nitrophenyl)piperidine-4-carboxamide (0.21 g), 84% yield. 1H NMR (500 MHz, DMSO): δ 1.51 (m, 2H), 1.74 (m, 2H), 2.48 (m, 1H), 2.96 (m, 2H), 3.93 (m, 2H), 4.26 (d, J=5.9 Hz, 2H), 4.59 (d, J=5.8 Hz, 2H), 5.95 (d, J=2.45 Hz, 1H), 6.42 (dd, J=2.5 Hz, 1H), 7.24 (m, 4H) 7.37 (m, 4H), 7.42 (m, 2H), 7.91 (d, J=9.7 Hz, 1H), 8.35 (m, 1H), 8.84 (m, 1H). HRMS (ESI) calculated for C26H28N4NaO3: 467.2054, Found: 467.2054.

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-9abea2b5359f4bf9a8a8d6ba3e53ac9e
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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