Triethylamine → HCID 18686761, compound

HRID 1872497Notes

Reaction equation

HRID 1872497 reaction equation
Cl[C:2]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[C:11]([Cl:18])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C.[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1>C1COCC1>[Cl:18][C:11]1[C:3]([CH2:4][N:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[C:2]([NH:33][CH2:32][C:31]2[CH:34]=[CH:35][C:28]([O:27][CH3:26])=[CH:29][CH:30]=2)[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 18686758HCID 18686758, compound

Product 1

HCID 18686761HCID 18686761, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2,6-dichloro-3-nitro-benzyl)-piperidine (21) (0.894 g, 3.09 mmol) and triethylamine (0.606 g, 6 mmol) in anhydrous THF (5 mL), p-methoxy benzylamine (0.823 g, 6 mmol) was added at 0° C. under stirring. The reaction mixture was allowed to warm to room temperature and stirred for additional 12 hours and evaporated to dryness. The product was extracted with EtOAc (100 mL) and washed with water (2×50 mL) and dried (MgSO4). The product was purified by column chromatography (SiO2, hexanes:EtOAc, 95:5 to 9:1) as a yellow oil. Yield: 0.81 g, 67%. 1H-NMR (CDCl3) δ 1.23-1.26 (m, 6H), 2.23 (m, 4H), 3.63 (s, 2H), 3.76 (s, 3H), 3.92 (d, 2H, J=4.4 Hz), 6.65 (d, 1H, J=9.04 Hz), 6.82 (d, 2H, J=8.6 Hz), 7.18 (d, 2H, J=8.6 Hz), 7.18 (d, 2H, J=8.6 Hz) 7.57 (d, 1H, J=9 Hz), 8.29 (bs, 1H). NOE's were observed from H4 to H3, H5, H6. No NOE was observed from H4 to H1, which would have been expected if the other regioisomer was formed. MS (CI) m/z 390 (M+1), 392 (M+2).

Workup

  1. stirringstirred for additional 12 hours
  2. customevaporated to dryness
  3. extractionThe product was extracted with EtOAc (100 mL)
  4. washwashed with water (2×50 mL)
  5. dry with materialdried (MgSO4)
  6. customThe product was purified by column chromatography (SiO2, hexanes:EtOAc, 95:5 to 9:1) as a yellow oil
  7. customwas formed

Sources & evidence

ORD record
ord-3db91b898a1a4ca49aea0287be5047bc
Source dataset
uspto-grants-2000_08
Patent number
US06110911

Reaction notes

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