Piperidine → HCID 178519951, compound

HRID 1611399Notes

Reaction equation

HRID 1611399 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:13][C:12]([C:14](Cl)=[O:15])=[N:11][C:10]=2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(N(CC)CC)C>ClCCl>[NH3:11].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:13][C:12]([C:14]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:15])=[N:11][C:10]=2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 178521129HCID 178521129, compound

Product 2

HCID 222AmmoniaHCID 178519951HCID 178519951, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product of Step 1 (52 mg, 0.15 mmol) was dissolved in anhydrous dichloromethane (3 ml), piperidine (0.025 ml, 0.23 mmol) was added followed by triethylamine (0.084 ml, 0.6 mmol) and the mixture stirred at room temperature for 2 hours. The mixture was diluted with dichloromethane and washed with aqueous sodium bicarbonate and brine. The organic layer was dried (MgSO4) and evaporated under vacuum. The residue was chromatographed on silica gel eluting with 5% of a 9:1 methanol:0.880 ammonia solution, in dichloromethane to give the title compound as a white solid (16 mg, 26%); MS(AP+) m/e 402 [M+H]+.

Workup

  1. washwashed with aqueous sodium bicarbonate and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated under vacuum
  4. customThe residue was chromatographed on silica gel eluting with 5% of a 9:1 methanol

Sources & evidence

ORD record
ord-aa14566ef6b645f8a21ee2d8977c8db5
Source dataset
uspto-grants-2006_01
Patent number
US06987119B2

Reaction notes

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