Hydrochloric Acid → 4,4-Dimethyl-1-(4-(4-(4-(1,1-dimethylethyl)-2-thiazolyl)-1-piperazinyl)butyl)-2,6-piperidin-dione

HRID 329606

Reaction equation

HRID 329606 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11](=[O:12])[CH2:10][C:9]([CH3:14])([CH3:13])[CH2:8][C:7]1=[O:15].[CH3:16][C:17]([C:20]1[N:21]=[C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[S:23][CH:24]=1)([CH3:19])[CH3:18].C([O-])([O-])=O.[K+].[K+].Cl>O.C(O)C.CCOCC.CN(C)C=O>[CH3:13][C:9]1([CH3:14])[CH2:10][C:11](=[O:12])[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:28]2[CH2:29][CH2:30][N:25]([C:22]3[S:23][CH:24]=[C:20]([C:17]([CH3:19])([CH3:18])[CH3:16])[N:21]=3)[CH2:26][CH2:27]2)[C:7](=[O:15])[CH2:8]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 136603351-(4-Bromobutyl)-4,4-dimethylpiperidine-2,6-dioneHCID 198712791-(4-(1,1-Dimethylethyl)-2-thiazolyl)-piperazine

Product 1

HCID 137477334,4-Dimethyl-1-(4-(4-(4-(1,1-dimethylethyl)-2-thiazolyl)-1-piperazinyl)butyl)-2,6-piperidin-dione

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 21585056Diethyl ether ethanolSolvent

Procedure

4 g 1-(4-Bromobutyl)-4,4-dimethyl-2,6-piperidin-dione, 3.15 g 1-(4-(1,1-dimethylethyl)-2-thiazolyl)-piperazine, 2.7 g K2CO3, 70 ml dimethylformamide and 20 ml water are stirred at room temperature for about 35 hours. The mixture is diluted with water, extracted twice with ether, the combined extracts are washed with water, dried (Na2SO4) and evaporated. The residue is recrystallized from hexane/ethyl acetate, whereby the title compound is obtained, m.p. 93°-94°. M.p. of the hydrochloride is 199°-201° (ethanol/ether).

Workup

  1. extractionextracted twice with ether
  2. washthe combined extracts are washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue is recrystallized from hexane/ethyl acetate, whereby the title compound
  6. customis obtained
  7. customis 199°-201°

Sources & evidence

ORD record
ord-5f01b3268e334e29afc05a72f5dd0b2e
Source dataset
uspto-grants-1990_01
Patent number
US04892879

Linked notes

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