Potassium Carbonate → HCID 67995893, compound

HRID 1615111Notes

Reaction equation

HRID 1615111 reaction equation
Cl[CH2:2][CH2:3][C:4]([OH:11])([CH2:8][CH:9]=[CH2:10])[CH2:5][CH:6]=[CH2:7].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]([NH2:21])[CH3:20])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]([NH:21][CH2:2][CH2:3][C:4]([OH:11])([CH2:8][CH:9]=[CH2:10])[CH2:5][CH:6]=[CH2:7])[CH3:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 641053HCID 641053, compoundHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamine

Product 1

HCID 67995893HCID 67995893, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(2-chloro-ethyl)-hepta-1,6-dien-4-ol (7.87 g), (S)-1-(4-bromo-phenyl)-ethylamine (13.52 g), K2CO3 (9.34 g), KI (8.23 g), and acetonitrile (150 mL) is stirred at reflux temperature overnight. After cooling to room temperature, the mixture is concentrated under reduced pressure and water is added to the residue. The resulting mixture is extracted with ethyl acetate (3×), and the combined extracts are washed with brine and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1) to afford the title compound as an oil. Yield: 8.36 g (55% of theory); Mass spectrum (ESI+): m/z=338/340 (Br) [M+H]+.

Workup

  1. temperatureat reflux temperature overnight
  2. concentrationthe mixture is concentrated under reduced pressure and water
  3. additionis added to the residue
  4. extractionThe resulting mixture is extracted with ethyl acetate (3×)
  5. washthe combined extracts are washed with brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent is evaporated
  8. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1)

Sources & evidence

ORD record
ord-b2641cd7cb9a449bbfa885b5c584fd7b
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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