Triethylamine → HCID 56777233, compound

HRID 1715123Notes

Reaction equation

HRID 1715123 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(N(CC)CC)C.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([NH:31][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 56777233HCID 56777233, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-chloro-3-nitro-pyridine (25.0 g, 157.69 mmol, 1.0 equiv; commercially available) and triethylamine (19.15 g, 189.23 mol, 1.2 equiv) in anhydrous DMF (100 mL) was added 4-amino-piperidine-1-carboxylic acid tert-butyl ester (31.58 g, 157.69 mmol, 1.0 equiv; commercially available), dissolved in anhydrous DMF (30 mL), and the reaction mixture stirred at rt for 15 h. The reaction mixture was poured into ice-cold water (1 L) and stirred for 2 h, allowed to settle for another 2 h and then filtered. The orange solid was washed with water and air-dried. The crude material was crystallized from ethyl acetate to obtain 43.7 g (86%) of the title compound. 1H NMR (400 MHz, DMSO): δ 1.41 (s, 9H), 1.48-1.56 (m, 2H), 1.88-1.90 (m, 2H), 2.93 (br s, 2H), 3.90-3.93 (m, 3H), 7.14 (d, J=6.3 HZ, 1H), 8.03 (d, J=7.9 Hz, 1H), 8.27 (s, J=6.2 Hz, 1H), 9.03 (s, 1H).

Workup

  1. stirringstirred for 2 h
  2. waitto settle for another 2 h
  3. filtrationfiltered
  4. washThe orange solid was washed with water
  5. customair-dried
  6. customThe crude material was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-c8b299374e3b4402bc84671db7a9501a
Source dataset
uspto-grants-2010_09
Patent number
US07799806B2

Reaction notes

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