Triethylamine → Hydrochloric Acid

HRID 1825899Notes

Reaction equation

HRID 1825899 reaction equation
[CH:1]1([CH2:7][C@@H:8]([NH2:24])[CH2:9][N:10]2[CH2:15][CH:14]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:32][C:33]1([C:39]([Cl:41])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>ClCCl>[CH:1]1([CH2:7][C@@H:8]([NH:24][C:39]([C:33]2([CH3:32])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)=[O:40])[CH2:9][N:10]2[CH2:11][CH:12]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH2:14][CH2:15]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:41]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 41892451-Methylcyclohexanecarbonyl chlorideHCID 12052824HCID 12052824, compound

Product 2

HCID 313Hydrochloric AcidHCID 12052817HCID 12052817, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 0.25 g (0.76 mmol) of {(1R)-1-cyclohexylmethyl-2-[4-(2-methoxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethyl}-amine and 0.21 mL (1.52 mmol) of triethylamine in 10 mL of dichloromethane at 0° C. was added dropwise 0.13 g (0.84 mmol) of 1-methyl-cyclohexanecarboxylic acid chloride in 4 mL of dichloromethane. The reaction mixture was allowed to stir under nitrogen at 0° C. for one hour, and was then concentrated on a rotary evaporator, diluted with ethyl acetate and washed with saturated aqueous NaHCO3 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 (dichloromethane/methanol) and then converted to the hydrochloride.hemihydrate salt of the title compound with ethanolic HCl to yield 0.15 g (41%) of yellow solid; mp=93–95° C.; MS (+) ESI m/z=453 (M+H)+.

Workup

  1. concentrationwas then concentrated on a rotary evaporator
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated aqueous NaHCO3 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 (dichloromethane/methanol)

Sources & evidence

ORD record
ord-205958e167d84127a436048b21a61fe3
Source dataset
uspto-grants-2006_05
Patent number
US07049330B2

Reaction notes

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