Water → HCID 11023122, compound

HRID 977165Notes

Reaction equation

HRID 977165 reaction equation
Br[CH2:2][CH:3]=[CH:4][C:5]#[C:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH3:11][N:12]([CH3:23])[CH2:13][C:14]([CH3:22])([CH3:21])[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:8][C:7]([CH3:10])([CH3:9])[C:6]#[C:5]/[CH:4]=[CH:3]/[CH2:2][N:18]1[CH2:19][CH2:20][CH:15]([C:14]([CH3:22])([CH3:21])[CH2:13][N:12]([CH3:11])[CH3:23])[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10921200Dimethyl[2-methyl-2-(piperidin-4-yl)propyl]amineHCID 454895941-Bromo-6,6-dimethylhept-2-en-4-yne

Product 1

HCID 11023122HCID 11023122, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

12 g (6.10-2 mole)of 1-bromo-6,6-dimethyl-2-hepten-4-yne (E/Z=3/1) in solution in 20 ml of N,N-dimethylformamide was added drop-wise to a mixture of 10 g (5.4×10-2 mole) of N,N,β,β-tetramethyl-4-piperidineethanamine and 14.9 g of potassium carbonate in 150 ml of N,N-dimethylformamide. The mixture was stirred for 48 hours at room temperature then poured into water. This was extracted several times with ethyl acetate. The organic phase was washed with water, dried over magnesium sulphate and filtered and the solvents were evaporated off under reduced pressure. The residual oil obtained was purified by silica column chromatography, eluting with a 9/1 (v/v) methylene chloride/methanol mixture. After evaporation of the solvents under reduced pressure, 10.3 g (yield: 56%) of (E)-1-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N,N,β,β-tetramethyl-4-piperidineethanamine was obtained. The corresponding (Z)-2-butene-dioate was obtained from this in ethanol. M Pt=185°-188° C.

Workup

  1. extractionThis was extracted several times with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvents were evaporated off under reduced pressure
  6. customThe residual oil obtained
  7. customwas purified by silica column chromatography
  8. washeluting with a 9/1 (v/v) methylene chloride/methanol mixture
  9. customAfter evaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-b582473769b14e5bad310c7e7c74ad0f
Source dataset
uspto-grants-1997_03
Patent number
US05614534

Reaction notes

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