Triethylamine → HCID 15896355, compound

HRID 131537Notes

Reaction equation

HRID 131537 reaction equation
Cl.[CH2:2]1[C:6]2([CH2:11][CH2:10][N:9]([NH2:12])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[C:30]3[N:31]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:38]=4[Cl:44])[N:32]=[C:33]([C:34](Cl)=[O:35])[C:29]=3[S:28][CH2:27][C:25]=2[CH:26]=1>C(Cl)Cl>[CH2:2]1[C:6]2([CH2:11][CH2:10][N:9]([NH:12][C:34]([C:33]3[C:29]4[S:28][CH2:27][C:25]5[CH:26]=[C:21]([Cl:20])[CH:22]=[CH:23][C:24]=5[C:30]=4[N:31]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:38]=4[Cl:44])[N:32]=3)=[O:35])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22394211168273-00-5HCID 87781311HCID 87781311, compound

Product 1

HCID 15896355HCID 15896355, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.28 g of 8-azaspiro[4.5]dec-8-ylamine hydrochloride and 0.41 ml of triethylamine in 15 ml of DCM is cooled to 0° C., 0.6 g of the acid chloride prepared in Example 1, step A, in 10 ml of DCM is added dropwise and the mixture is left for 4 hours, with stirring, at RT. The mixture is extracted with DCM, the organic phase is washed with water, with a saturated NaCl solution, dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, eluting with the toluene/AcOEt (95/5; v/v) mixture. 0.45 g of the expected compound is obtained in amorphous form.

Workup

  1. extractionThe mixture is extracted with DCM
  2. washthe organic phase is washed with water, with a saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customthe solvent is evaporated under vacuum
  5. customThe residue is chromatographed on silica gel
  6. washeluting with the toluene/AcOEt (95/5; v/v) mixture

Sources & evidence

ORD record
ord-b1ee6c95a19d42fe8863c76533a8e4ff
Source dataset
uspto-grants-2008_06
Patent number
US07384960B2

Reaction notes

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