Triethylamine → HCID 12052800, compound

HRID 842631Notes

Reaction equation

HRID 842631 reaction equation
[CH:1]1([CH2:7][C@@H:8]([NH:26][CH3:27])[CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:25]4[O:24][CH2:23][CH2:22][O:21][C:20]=4[CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:35][C:36]1([C:42](Cl)=[O:43])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>ClCCl>[CH:1]1([CH2:7][C@@H:8]([N:26]([CH3:27])[C:42]([C:36]2([CH3:35])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[O:43])[CH2:9][N:10]2[CH2:11][CH2:12][N:13]([C:16]3[C:25]4[O:24][CH2:23][CH2:22][O:21][C:20]=4[CH:19]=[CH:18][CH:17]=3)[CH2:14][CH2:15]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 41892451-Methylcyclohexanecarbonyl chlorideHCID 12052818HCID 12052818, compound

Product 1

HCID 12052800HCID 12052800, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.7 g (1.87 mmol) of {(1R)-1-cyclohexylmethyl-2-[4-(2,3dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-ethyl}-methyl-amine and 0.5 mL (3.7 mmol) of triethylamine in 10 mL of dichloromethane at 0° C. was added dropwise 0.3 g (1.87 mmol) of 1-methyl-cyclohexanecarboxylic acid chloride in dichloromethane. The reaction mixture was allowed to stir under nitrogen overnight at ambient temperature and was then concentrated on a rotary evaporator, diluted with ethyl acetate and washed with H2O and brine. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator to yield the crude product, which was purified by flash chromatography on silica gel (ethyl acetate/hexanes) and converted to the hydrochloride salt of the title compound with ethereal HCl to yield 0.85 g (91%) of the title compound as a white solid; mp=219-220° C.; MS(+)ESI m/z=498 (M+H)+.

Workup

  1. concentrationwas then concentrated on a rotary evaporator
  2. additiondiluted with ethyl acetate
  3. washwashed with H2O and brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator
  7. customto yield the crude product, which
  8. customwas purified by flash chromatography on silica gel (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1fa4e7a2013941a2a79f36142cb223af
Source dataset
uspto-grants-2002_04
Patent number
US06376494B1

Reaction notes

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