Diisopropylethylamine → HCID 131730291, compound

HRID 1944653Notes

Reaction equation

HRID 1944653 reaction equation
[Cl:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:13]1[NH:18][CH2:17][CH2:16][N:15]2[CH2:19][CH2:20][CH2:21][CH2:22][CH:14]12.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.CS(C)=O>[ClH:1].[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([N:18]3[CH2:17][CH2:16][N:15]4[CH2:19][CH2:20][CH2:21][CH2:22][CH:14]4[CH2:13]3)[S:3][C:4]=2[CH:10]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2731322-Chloro-6-methoxybenzothiazoleHCID 516892Sodium BicarbonateHCID 2876391(+-)-1,4-Diazabicyclo[4.4.0]decane

Product 1

HCID 131730291HCID 131730291, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 2-chloro-6-methoxybenzothiazole (0.17 g, 1.0 mmol), octahydropyrido[1,2-a]-pyrazine (0.21 g, 1.0 mmol), DIPEA (0.51 mL) and dimethylsulfoxide (1 mL) was stirred at 115° C. overnight. The reaction mixture was allowed to cool and dissolved in a mixture of ethyl acetate and a NaHCO3 solution. The phases were separated and the organic phase was washed with water (3×) and then extracted with 0.25 M hydrochloric acid (20 mL). The acidic aqueous extract was concentrated and re-evaporated with ethanol. The residue was crystallized from a mixture of ethanol and ethyl acetate to give 193 mg (57%) of 2-(6-methoxybenzothiazol-2-yl)octahydropyrido[1,2-a]pyrazine, hydrochloride.

Workup

  1. temperatureto cool
  2. customThe phases were separated
  3. washthe organic phase was washed with water (3×)
  4. extractionextracted with 0.25 M hydrochloric acid (20 mL)
  5. extractionThe acidic aqueous extract
  6. concentrationwas concentrated
  7. customre-evaporated with ethanol
  8. customThe residue was crystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-63e6fa3d48274024bd3f5deba8de389b
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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