Triethylamine → HCID 178501230, compound

HRID 2390992Notes

Reaction equation

HRID 2390992 reaction equation
Cl.[CH3:2][O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([NH2:12])[CH2:8][CH2:7]1)=[O:5].C(N(CC)CC)C.[Cl:20][C:21]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:22]=1[C:23](Cl)=[O:24]>C1COCC1.O.C(OCC)(=O)C>[CH3:2][O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:23](=[O:24])[C:22]2[CH:26]=[C:27]([C:30]([F:31])([F:32])[F:33])[CH:28]=[CH:29][C:21]=2[Cl:20])[CH2:8][CH2:7]1)=[O:5]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27781062-Chloro-5-(trifluoromethyl)benzoyl chlorideHCID 178501210HCID 178501210, compound

Product 1

HCID 178501230HCID 178501230, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of trans-4-amino-cyclohexylcarboxylic acid methyl ester hydrochloride (6.7 g, 34.7 mmol) in dry THF (90 mL) under nitrogen atmosphere is added triethylamine (12 mL, 86.8 mmol). The suspension is cooled to 0° C. and 2-chloro-5-(trifluoromethyl)benzoyl chloride (8.85 g, 36.4 mmol) in dry THF (40 mL) is added dropwise over 20 minutes. The resulting thick, colourless slurry is stirred at 0-5° C. for 30 minutes and then allowed to warm to room temp and stirred at room temp for 1 hour. The reaction is quenched by the dropwise addition of water (5 mL) in THF (45 mL) to give a clear solution. This is diluted with water (100 mL) and ethyl acetate (300 mL). The biphasic mixture is stirred for 5 minutes then the organic phase is separated and washed successively with water (100 mL), saturated sodium bicarbonate (100 mL) and saturated brine (100 mL), dried (MgSO4), filtered and evaporated to give a colourless solid.; [MH+ 364].

Workup

  1. temperatureto warm to room temp
  2. stirringstirred at room temp for 1 hour
  3. customThe reaction is quenched by the dropwise addition of water (5 mL) in THF (45 mL)
  4. customto give a clear solution
  5. stirringThe biphasic mixture is stirred for 5 minutes
  6. customthe organic phase is separated
  7. washwashed successively with water (100 mL), saturated sodium bicarbonate (100 mL) and saturated brine (100 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto give a colourless solid

Sources & evidence

ORD record
ord-a17dfab1de5a4dbcba870eedc1acbdd8
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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